31:
3443:
934:
because they are not fully absorbed in the small intestine. Some individuals experience such symptoms even in a single-serving quantity. With continued use, most people develop a degree of tolerance to sugar alcohols and no longer experience these symptoms.
1068:
Honkala S, Runnel R, Saag M, Olak J, Nõmmela R, Russak S, Mäkinen PL, Vahlberg T, Falony G, Mäkinen K, Honkala E (May 21, 2014). "Effect of erythritol and xylitol on dental caries prevention in children".
1193:"Gastrointestinal Disturbances Associated with the Consumption of Sugar Alcohols with Special Consideration of Xylitol: Scientific Review and Instructions for Dentists and Other Health-Care Professionals"
959:
Hubert
Schiweck; Albert Bär; Roland Vogel; Eugen Schwarz; Markwart Kunz; Cécile Dusautois; Alexandre Clement; Caterine Lefranc; Bernd Lüssem; Matthias Moser; Siegfried Peters (2012). "Sugar Alcohols".
95:
Sugar alcohols are used widely in the food industry as thickeners and sweeteners. In commercial foodstuffs, sugar alcohols are commonly used in place of table sugar (
178:(six-carbon sugars), which are the more common sugars. They have one −OH group attached to each carbon. They are further differentiated by the relative orientation (
1415:
858:
In addition to their sweetness, some sugar alcohols can produce a noticeable cooling sensation in the mouth when highly concentrated, for instance in sugar-free
2106:
2096:
2091:
2805:
2348:
2116:
2111:
2101:
2034:
2024:
2018:
2363:
2353:
2086:
2076:
2044:
2039:
2029:
1030:
Bradshaw, D.J.; Marsh, P.D. (1994). "Effect of Sugar
Alcohols on the Composition and Metabolism of a Mixed Culture of Oral Bacteria Grown in a Chemostat".
170:. Like their parent sugars, sugar alcohols exist in diverse chain length. Most have five- or six-carbon chains, because they are derived respectively from
992:
Ruppert, Agnieszka M.; Weinberg, Kamil; Palkovits, Regina (2012). "Hydrogenolysis Goes Bio: From
Carbohydrates and Sugar Alcohols to Platform Chemicals".
2790:
2241:
2081:
2013:
2002:
182:) of these −OH groups. Unlike sugars, which tend to exist as rings, sugar alcohols do not, although they can be dehydrated to give cyclic ethers (e.g.
2071:
3044:
2785:
1947:
914:
is actually absorbed in the small intestine and excreted unchanged through urine, so it contributes no calories even though it is rather sweet.
3049:
3039:
1936:
1297:
1270:
1175:
1149:
976:
80:
attached to each carbon atom. They are white, water-soluble solids that can occur naturally or be produced industrially by
479:
can form sugar alcohols; however, sugar alcohols derived from disaccharides (e.g. maltitol and lactitol) are not entirely
17:
1391:
3394:
3194:
615:
3423:
882:
is due to the dissolution of the sugar alcohol being an endothermic (heat-absorbing) reaction, one with a strong
3289:
2383:
2326:
499:
of the most widely used sugar alcohols. Despite the variance in food energy content of sugar alcohols, the
3337:
1689:
1561:
883:
3472:
3399:
2698:
1629:
1624:
3418:
3409:
3389:
1619:
2743:
922:
Like many other incompletely digestible substances, overconsumption of sugar alcohols can lead to
3467:
3274:
2640:
3279:
1664:
1614:
1609:
1384:
65:
1287:
1260:
1165:
1139:
836:
than sucrose. Their flavor is similar to sucrose, and they can be used to mask the unpleasant
3314:
2703:
1351:
1243:
907:
270:
is no longer obtained from natural sources; currently, sorbitol and mannitol are obtained by
331:
Sugar alcohols are absorbed at 50% of the rate of sugars, resulting in less of an effect on
3404:
1701:
1674:
100:
8:
3428:
2780:
2723:
2685:
2358:
2343:
2321:
1669:
1581:
1481:
1400:
1313:
Cammenga, HK; LO Figura; B Zielasko (1996). "Thermal behaviour of some sugar alcohols".
3342:
3323:
3199:
2815:
2660:
2655:
2650:
2645:
2400:
2266:
1732:
1571:
1463:
1430:
1330:
1219:
1192:
1094:
199:
847:
Sugar alcohols are not metabolized by oral bacteria, and so they do not contribute to
278:
catalysts. The conversion of glucose and mannose to sorbitol and mannitol is given as
3446:
3377:
3298:
2810:
2413:
2392:
2368:
2316:
2311:
2214:
2194:
2184:
2174:
2169:
1654:
1586:
1522:
1455:
1450:
1377:
1293:
1266:
1224:
1171:
1145:
1086:
1047:
1009:
972:
903:
879:
503:'s labeling requirements assign a blanket value of 2.4 kcal/g to all sugar alcohols.
3318:
1334:
832:
As a group, sugar alcohols are not as sweet as sucrose, and they have slightly less
2847:
2795:
2738:
2565:
2512:
2408:
2306:
2209:
2179:
2159:
2149:
2007:
1659:
1322:
1214:
1204:
1098:
1078:
1039:
1001:
964:
841:
61:
968:
958:
902:
than "regular" sugar (sucrose). This property makes them popular sweeteners among
3382:
3351:
3284:
3251:
3204:
3189:
2857:
2551:
2546:
2507:
2231:
2199:
2164:
1714:
1649:
1644:
1639:
1634:
1576:
1541:
1440:
895:
349:
179:
894:
Sugar alcohols are usually incompletely absorbed into the blood stream from the
3413:
3328:
3184:
2733:
2693:
2378:
2154:
2144:
2139:
2129:
1996:
1958:
1941:
1925:
1881:
1870:
1864:
1709:
1604:
1494:
527:
500:
484:
476:
336:
225:
3461:
3367:
3266:
2800:
2772:
2715:
2486:
2373:
2301:
2296:
2134:
1969:
1963:
1952:
1892:
1886:
1875:
1566:
1514:
1489:
899:
271:
247:
234:
211:
81:
3256:
2632:
2291:
1859:
1684:
1228:
1209:
1090:
1013:
1005:
803:
480:
472:
309:
275:
1051:
3372:
3346:
3236:
3083:
2675:
2670:
2665:
2456:
1930:
1853:
1847:
867:
863:
848:
833:
518:
496:
332:
325:
37:
is a sugar alcohol. It is 60–70% as sweet as sugar and almost noncaloric.
3333:
3246:
3241:
3146:
2947:
2877:
2753:
2575:
2476:
2286:
2281:
2251:
2246:
2204:
1919:
1802:
1792:
1782:
1737:
1471:
1445:
1425:
1326:
931:
911:
852:
837:
565:
403:
361:
305:
187:
34:
30:
1082:
1043:
3141:
3131:
3113:
2967:
2758:
2613:
2466:
2276:
2271:
2261:
2256:
2236:
1841:
1813:
1807:
1797:
1787:
1742:
427:
207:
1241:
3220:
3136:
3108:
3093:
3088:
3029:
3024:
3008:
2937:
2927:
2897:
2887:
2867:
2603:
2599:
2579:
2561:
2528:
2436:
1772:
1553:
1527:
927:
923:
875:
871:
815:
814:
is 100 and sucrose is 60–68. = Sugars, like glucose, sucrose, and
807:
745:
720:
695:
670:
590:
540:
445:
439:
421:
397:
391:
373:
367:
355:
267:
216:
183:
108:
73:
335:
levels as measured by comparing their effect to sucrose using the
137:. In contrast, sugars have two fewer hydrogen atoms, for example,
3098:
3078:
3034:
2990:
2917:
2907:
2748:
2728:
2589:
2446:
1777:
1724:
1679:
1596:
1502:
1435:
1258:
811:
799:
770:
645:
433:
409:
385:
379:
313:
171:
104:
96:
3164:
2957:
2189:
415:
203:
175:
89:
1248:. Am Cncl on Science, Health. pp. 14–. GGKEY:2Q64ACGKWRT.
3103:
859:
69:
1369:
1312:
1141:
The
Technology of Wafers and Waffles I: Operational Aspects
1252:
991:
616:
1285:
1279:
889:
1170:. Elsevier Science. 22 November 2018. pp. 266–.
1067:
1262:
1137:
198:
Sugar alcohols can be, and often are, produced from
490:
870:phase of sorbitol, erythritol, xylitol, mannitol,
3459:
1259:Kay O'Donnell; Malcolm Kearsley (13 July 2012).
1235:
1115:, p. 79, 10th ed., Bull Publishing Company, 2011
111:are popular sugar alcohols in commercial foods.
1242:Kathleen A. Meister; Marjorie E. Doyle (2009).
1131:
898:which generally results in a smaller change in
495:This table presents the relative sweetness and
1063:
1061:
961:Ullmann's Encyclopedia of Industrial Chemistry
806:, including sugars like glucose, sucrose, and
1385:
1029:
532:Maximum non-laxative dose (g/kg body weight)
99:), often in combination with high-intensity
1265:. John Wiley & Sons. pp. 322–324.
1184:
1158:
1058:
1025:
1023:
1392:
1378:
103:, in order to offset their low sweetness.
1218:
1208:
1128:, p. 124, 1st ed., Everything Books, 2004
954:
952:
950:
948:
1346:
1344:
1020:
621:Tooltip Hydrogenated starch hydrolysates
342:
262:
119:Sugar alcohols have the general formula
29:
1286:Lyn O'Brien-Nabors (6 September 2011).
1190:
1113:Diabetes Mellitus: A Practical Handbook
994:Angewandte Chemie International Edition
328:; in fact, xylitol deters tooth decay.
214:; the main conversion technologies use
14:
3460:
1289:Alternative Sweeteners, Fourth Edition
945:
866:. This happens, for example, with the
1373:
1341:
2539:Polyhydric alcohols (sugar alcohols)
1138:Karl F. Tiefenbacher (16 May 2017).
810:, are ~4.0 kcal/g and 100%. =
461:
324:Sugar alcohols do not contribute to
84:sugars. Since they contain multiple
1354:. Yale New Haven Health. 2005-03-10
1144:. Elsevier Science. pp. 165–.
1111:Sue Milchovich, Barbara Dunn-Long:
890:Absorption from the small intestine
255:double bonds, converting sugars to
24:
827:
424:(6-carbon; a cyclic sugar alcohol)
25:
3484:
3195:2-Methyl-2-propyl-1,3-propanediol
319:
3442:
3441:
491:Sugar alcohols as food additives
3424:Nucleophilic conjugate addition
1352:"Eat Any Sugar Alcohol Lately?"
1306:
1124:Paula Ford-Martin, Ian Blumer:
917:
505:
287:CH(OH)CH(OH)CH(OH)CH(OH)CHO + H
88:groups, they are classified as
1167:Encyclopedia of Food Chemistry
1118:
1105:
985:
13:
1:
3395:Fischer–Speier esterification
2327:Propylene glycol methyl ether
969:10.1002/14356007.a25_413.pub3
938:
507:Properties of sugar alcohols
300:
295:CH(OH)CH(OH)CH(OH)CH(OH)CHHOH
193:
1399:
1292:. CRC Press. pp. 259–.
1126:The Everything Diabetes Book
487:is available for reduction.
202:. Particular feedstocks are
114:
7:
1562:4-Methylcyclohexanemethanol
1315:Journal of Thermal Analysis
1245:Obesity and Food Technology
10:
3489:
3400:Williamson ether synthesis
2699:2,4-Dichlorobenzyl alcohol
1630:2-(2-Methoxyethoxy)ethanol
1625:2-(2-Methoxyethoxy)ethanol
454:Maltotetraitol (24-carbon)
245:to smaller molecules, and
3437:
3419:Friedel-Crafts alkylation
3410:Nucleophilic substitution
3390:Nucleophilic substitution
3360:
3307:
3265:
3229:
3213:
3177:
3155:
3122:
3069:
3062:
3017:
2999:
2981:
2833:
2824:
2767:
2712:
2684:
2631:
2537:
2521:
2500:
2429:
2422:
2334:
2223:
2053:
1978:
1901:
1823:
1754:
1723:
1620:2-(2-Ethoxyethoxy)ethanol
1595:
1552:
1540:
1513:
1480:
1414:
1407:
794:
241:single bonds, converting
174:(five-carbon sugars) and
2641:2,2-Dimethylpropan-1-ol
1697:-Diisopropylaminoethanol
524:Relative food energy (%)
451:Maltotriitol (18-carbon)
3275:1,3-Difluoro-2-propanol
963:. Weinheim: Wiley-VCH.
851:. They do not brown or
840:of some high-intensity
3280:2,2,2-Trifluoroethanol
1665:Aminoethylethanolamine
1615:2,2,2-Trifluoroethanol
1610:2,2,2-Trichloroethanol
1006:10.1002/anie.201105125
908:low-carbohydrate diets
515:Relative sweetness (%)
38:
2704:3-Nitrobenzyl alcohol
343:Common sugar alcohols
263:Sorbitol and mannitol
186:can be dehydrated to
101:artificial sweeteners
33:
3405:Elimination reaction
2107:1-Heptatetracontanol
2097:1-Pentatetracontanol
2092:1-Tetratetracontanol
1999:(melissyl / myricyl)
1966:(cluytyl / montanyl)
1675:Dimethylethanolamine
1210:10.1155/2016/5967907
3429:Transesterification
2806:Palmitoleyl alcohol
2781:3-Methyl-3-pentanol
2724:Cetostearyl alcohol
2661:3-Methylbutan-2-ol
2656:3-Methylbutan-1-ol
2651:2-Methylbutan-2-ol
2646:2-Methylbutan-1-ol
2430:Monohydric alcohols
2359:3-Methyl-3-pentanol
2349:2-Methylheptan-2-ol
2344:2-Methyl-2-pentanol
2117:1-Nonatetracontanol
2112:1-Octatetracontanol
2102:1-Hexatetracontanol
2035:1-Heptatriacontanol
2025:1-Pentatriacontanol
2019:1-Tetratriacontanol
1705:-Methylethanolamine
1670:Diethylethanolamine
1582:Methylazoxymethanol
1499:Methanol poisoning
1191:Mäkinen KK (2016).
910:. As an exception,
508:
308:is obtained by the
200:renewable resources
46:polyhydric alcohols
18:Polyhydric alcohols
3324:Carbonyl reduction
3200:Diethylpropanediol
2816:tert-Butyl alcohol
2522:Trihydric alcohols
2364:3-Methyloctan-3-ol
2354:2-Methylhexan-2-ol
2267:3-Methyl-2-butanol
2087:1-Tritetracontanol
2077:1-Hentetracontanol
2045:1-Nonatriacontanol
2040:1-Octatriacontanol
2030:1-Hexatriacontanol
1878:(cetyl / palmityl)
1733:2-Methyl-1-butanol
1572:Cyclohexylmethanol
1431:2-Methyl-1-butanol
1327:10.1007/BF01983984
506:
39:
3473:Sugar substitutes
3455:
3454:
3378:Alcohol oxidation
3299:Trifluoromethanol
3173:
3172:
3058:
3057:
2811:tert-Amyl alcohol
2791:Linolenyl alcohol
2686:Aromatic alcohols
2627:
2626:
2501:Dihydric alcohols
2414:Triphenylmethanol
2369:Diacetone alcohol
2317:Pinacolyl alcohol
2242:2-Deoxyerythritol
2215:Veratrole alcohol
2195:Propargyl alcohol
2185:Phenethyl alcohol
2175:Nicotinyl alcohol
2170:Neopentyl alcohol
2125:
2124:
2082:1-Dotetracontanol
2014:1-Tritriacontanol
2003:1-Hentriacontanol
1655:2-Mercaptoethanol
1587:Trifluoromethanol
1536:
1535:
1523:Isopropyl alcohol
1451:Phenethyl alcohol
1416:Alcohols found in
1299:978-1-4398-4614-8
1272:978-1-118-37397-2
1177:978-0-12-814045-1
1151:978-0-12-811452-0
1083:10.1159/000358399
1044:10.1159/000261977
1000:(11): 2564–2601.
978:978-3-527-30673-2
880:cooling sensation
825:
824:
483:because only one
468:
467:
274:of sugars, using
72:, containing one
62:organic compounds
27:Organic compounds
16:(Redirected from
3480:
3445:
3444:
3067:
3066:
3063:Terpene alcohols
2848:Methylene glycol
2831:
2830:
2796:Linoleyl alcohol
2739:Myristyl alcohol
2566:Propylene glycol
2513:Propylene glycol
2427:
2426:
2409:Triphenylethanol
2322:Pirkle's alcohol
2307:Diphenylmethanol
2210:Vanillyl alcohol
2180:Perillyl alcohol
2160:Furfuryl alcohol
2150:Cinnamyl alcohol
2008:1-Dotriacontanol
1660:2-Methoxyethanol
1550:
1549:
1418:alcoholic drinks
1412:
1411:
1394:
1387:
1380:
1371:
1370:
1364:
1363:
1361:
1359:
1348:
1339:
1338:
1310:
1304:
1303:
1283:
1277:
1276:
1256:
1250:
1249:
1239:
1233:
1232:
1222:
1212:
1188:
1182:
1181:
1162:
1156:
1155:
1135:
1129:
1122:
1116:
1109:
1103:
1102:
1065:
1056:
1055:
1027:
1018:
1017:
989:
983:
982:
956:
884:heat of solution
622:
618:
509:
462:
296:
254:
240:
223:as the reagent:
222:
169:
150:
136:
87:
79:
21:
3488:
3487:
3483:
3482:
3481:
3479:
3478:
3477:
3458:
3457:
3456:
3451:
3433:
3383:Glycol cleavage
3356:
3352:Ziegler process
3303:
3285:2-Fluoroethanol
3261:
3225:
3209:
3205:Ethylene glycol
3190:1,5-Pentanediol
3169:
3157:
3151:
3124:
3118:
3071:
3054:
3018:Glycylglycitols
3013:
3001:
2995:
2983:
2977:
2973:
2963:
2953:
2943:
2933:
2923:
2913:
2903:
2893:
2883:
2873:
2863:
2858:Ethylene glycol
2853:
2841:
2837:
2820:
2771:
2769:
2763:
2714:
2708:
2680:
2623:
2619:
2609:
2595:
2585:
2571:
2557:
2552:Ethylene glycol
2547:Pentaerythritol
2533:
2517:
2508:Ethylene glycol
2496:
2492:
2482:
2472:
2462:
2452:
2442:
2423:Hydric alcohols
2418:
2336:
2330:
2232:1-Phenylethanol
2225:
2219:
2200:Salicyl alcohol
2165:Isoamyl alcohol
2121:
2072:1-Tetracontanol
2065:
2061:
2057:
2055:
2049:
1990:
1986:
1982:
1980:
1974:
1913:
1909:
1905:
1903:
1897:
1835:
1831:
1827:
1825:
1819:
1766:
1762:
1758:
1756:
1750:
1719:
1715:Tribromoethanol
1650:2-Fluoroethanol
1645:2-Ethoxyethanol
1640:2-Chloroethanol
1635:2-Butoxyethanol
1591:
1577:Methoxymethanol
1543:
1532:
1509:
1482:Medical alcohol
1476:
1441:Isoamyl alcohol
1417:
1403:
1398:
1368:
1367:
1357:
1355:
1350:
1349:
1342:
1311:
1307:
1300:
1284:
1280:
1273:
1257:
1253:
1240:
1236:
1189:
1185:
1178:
1164:
1163:
1159:
1152:
1136:
1132:
1123:
1119:
1110:
1106:
1066:
1059:
1032:Caries Research
1028:
1021:
990:
986:
979:
957:
946:
941:
920:
896:small intestine
892:
830:
828:Characteristics
620:
535:Dental acidity
493:
477:monosaccharides
469:
350:Ethylene glycol
345:
322:
312:of glucose and
303:
294:
290:
286:
282:
265:
252:
238:
220:
215:
196:
180:stereochemistry
167:
163:
156:
152:
148:
142:
138:
134:
130:
124:
120:
117:
85:
77:
28:
23:
22:
15:
12:
11:
5:
3486:
3476:
3475:
3470:
3468:Sugar alcohols
3453:
3452:
3450:
3449:
3438:
3435:
3434:
3432:
3431:
3426:
3421:
3416:
3414:carbonyl group
3407:
3402:
3397:
3392:
3387:
3386:
3385:
3375:
3370:
3364:
3362:
3358:
3357:
3355:
3354:
3349:
3340:
3331:
3329:Ether cleavage
3326:
3321:
3311:
3309:
3305:
3304:
3302:
3301:
3296:
3294:-butyl alcohol
3287:
3282:
3277:
3271:
3269:
3267:Fluoroalcohols
3263:
3262:
3260:
3259:
3254:
3249:
3244:
3239:
3233:
3231:
3227:
3226:
3224:
3223:
3217:
3215:
3211:
3210:
3208:
3207:
3202:
3197:
3192:
3187:
3185:1,4-Butanediol
3181:
3179:
3175:
3174:
3171:
3170:
3168:
3167:
3161:
3159:
3153:
3152:
3150:
3149:
3144:
3139:
3134:
3128:
3126:
3120:
3119:
3117:
3116:
3111:
3106:
3101:
3096:
3091:
3086:
3081:
3075:
3073:
3064:
3060:
3059:
3056:
3055:
3053:
3052:
3047:
3045:Maltotetraitol
3042:
3037:
3032:
3027:
3021:
3019:
3015:
3014:
3012:
3011:
3005:
3003:
2997:
2996:
2994:
2993:
2987:
2985:
2979:
2978:
2976:
2975:
2971:
2965:
2961:
2955:
2951:
2945:
2941:
2935:
2931:
2925:
2921:
2915:
2911:
2905:
2901:
2895:
2891:
2885:
2881:
2875:
2871:
2865:
2861:
2855:
2851:
2844:
2842:
2839:
2835:
2828:
2826:Sugar alcohols
2822:
2821:
2819:
2818:
2813:
2808:
2803:
2798:
2793:
2788:
2786:Erucyl alcohol
2783:
2777:
2775:
2773:fatty alcohols
2765:
2764:
2762:
2761:
2756:
2751:
2746:
2741:
2736:
2734:Lauryl alcohol
2731:
2726:
2720:
2718:
2716:fatty alcohols
2710:
2709:
2707:
2706:
2701:
2696:
2694:Benzyl alcohol
2690:
2688:
2682:
2681:
2679:
2678:
2673:
2668:
2663:
2658:
2653:
2648:
2643:
2637:
2635:
2629:
2628:
2625:
2624:
2622:
2621:
2617:
2611:
2607:
2597:
2593:
2587:
2583:
2573:
2569:
2559:
2555:
2549:
2543:
2541:
2535:
2534:
2532:
2531:
2525:
2523:
2519:
2518:
2516:
2515:
2510:
2504:
2502:
2498:
2497:
2495:
2494:
2490:
2484:
2480:
2474:
2470:
2464:
2460:
2454:
2450:
2444:
2440:
2433:
2431:
2424:
2420:
2419:
2417:
2416:
2411:
2406:
2404:-Butyl alcohol
2398:
2390:
2388:-butyl alcohol
2381:
2379:Methylpentynol
2376:
2371:
2366:
2361:
2356:
2351:
2346:
2340:
2338:
2332:
2331:
2329:
2324:
2319:
2314:
2309:
2304:
2299:
2294:
2289:
2284:
2279:
2274:
2269:
2264:
2259:
2254:
2249:
2244:
2239:
2234:
2229:
2227:
2221:
2220:
2218:
2217:
2212:
2207:
2202:
2197:
2192:
2187:
2182:
2177:
2172:
2167:
2162:
2157:
2155:Crotyl alcohol
2152:
2147:
2145:Benzyl alcohol
2142:
2140:Anisyl alcohol
2137:
2132:
2130:2-Ethylhexanol
2126:
2123:
2122:
2120:
2119:
2114:
2109:
2104:
2099:
2094:
2089:
2084:
2079:
2074:
2068:
2066:
2063:
2059:
2054:Straight-chain
2051:
2050:
2048:
2047:
2042:
2037:
2032:
2027:
2022:
2016:
2011:
2005:
2000:
1997:1-Triacontanol
1993:
1991:
1988:
1984:
1979:Straight-chain
1976:
1975:
1973:
1972:
1967:
1961:
1959:1-Heptacosanol
1956:
1950:
1948:1-Pentacosanol
1945:
1942:1-Tetracosanol
1939:
1934:
1928:
1926:1-Heneicosanol
1923:
1916:
1914:
1911:
1907:
1902:Straight-chain
1899:
1898:
1896:
1895:
1890:
1884:
1882:1-Heptadecanol
1879:
1873:
1871:1-Pentadecanol
1868:
1865:1-Tetradecanol
1862:
1857:
1851:
1845:
1838:
1836:
1833:
1829:
1824:Straight-chain
1821:
1820:
1818:
1817:
1811:
1805:
1800:
1795:
1790:
1785:
1780:
1775:
1769:
1767:
1764:
1760:
1755:Straight-chain
1752:
1751:
1749:
1748:
1740:
1735:
1729:
1727:
1721:
1720:
1718:
1717:
1712:
1710:Phenoxyethanol
1707:
1699:
1687:
1682:
1677:
1672:
1667:
1662:
1657:
1652:
1647:
1642:
1637:
1632:
1627:
1622:
1617:
1612:
1607:
1605:1-Aminoethanol
1601:
1599:
1593:
1592:
1590:
1589:
1584:
1579:
1574:
1569:
1564:
1558:
1556:
1547:
1538:
1537:
1534:
1533:
1531:
1530:
1525:
1519:
1517:
1515:Toxic alcohols
1511:
1510:
1508:
1507:
1506:
1505:
1497:
1495:Methylpentynol
1492:
1486:
1484:
1478:
1477:
1475:
1474:
1469:
1467:-Butyl alcohol
1461:
1453:
1448:
1443:
1438:
1433:
1428:
1422:
1420:
1409:
1408:By consumption
1405:
1404:
1397:
1396:
1389:
1382:
1374:
1366:
1365:
1340:
1321:(2): 427–434.
1305:
1298:
1278:
1271:
1251:
1234:
1183:
1176:
1157:
1150:
1130:
1117:
1104:
1057:
1038:(4): 251–256.
1019:
984:
977:
943:
942:
940:
937:
919:
916:
906:and people on
891:
888:
829:
826:
823:
822:
792:
791:
788:
785:
782:
779:
776:
773:
767:
766:
763:
760:
757:
754:
751:
748:
742:
741:
738:
735:
732:
729:
726:
723:
717:
716:
713:
710:
707:
704:
701:
698:
692:
691:
688:
685:
682:
679:
676:
673:
667:
666:
663:
660:
657:
654:
651:
648:
642:
641:
638:
635:
632:
629:
626:
623:
612:
611:
608:
605:
602:
599:
596:
593:
587:
586:
583:
580:
577:
574:
571:
568:
562:
561:
558:
555:
552:
549:
546:
543:
537:
536:
533:
530:
528:Glycemic index
525:
522:
516:
513:
501:European Union
492:
489:
485:aldehyde group
466:
465:
459:
458:
455:
452:
449:
443:
437:
431:
425:
419:
413:
407:
401:
395:
389:
383:
377:
371:
365:
359:
353:
346:
344:
341:
337:glycemic index
321:
320:Health effects
318:
302:
299:
298:
297:
292:
288:
284:
264:
261:
257:sugar alcohols
226:hydrogenolysis
218:
195:
192:
165:
158:
154:
144:
140:
132:
126:
122:
116:
113:
42:Sugar alcohols
26:
9:
6:
4:
3:
2:
3485:
3474:
3471:
3469:
3466:
3465:
3463:
3448:
3440:
3439:
3436:
3430:
3427:
3425:
3422:
3420:
3417:
3415:
3411:
3408:
3406:
3403:
3401:
3398:
3396:
3393:
3391:
3388:
3384:
3381:
3380:
3379:
3376:
3374:
3371:
3369:
3368:Deprotonation
3366:
3365:
3363:
3359:
3353:
3350:
3348:
3344:
3341:
3339:
3335:
3332:
3330:
3327:
3325:
3322:
3320:
3316:
3313:
3312:
3310:
3306:
3300:
3297:
3295:
3293:
3288:
3286:
3283:
3281:
3278:
3276:
3273:
3272:
3270:
3268:
3264:
3258:
3255:
3253:
3250:
3248:
3245:
3243:
3240:
3238:
3235:
3234:
3232:
3228:
3222:
3219:
3218:
3216:
3212:
3206:
3203:
3201:
3198:
3196:
3193:
3191:
3188:
3186:
3183:
3182:
3180:
3176:
3166:
3163:
3162:
3160:
3154:
3148:
3145:
3143:
3140:
3138:
3135:
3133:
3130:
3129:
3127:
3123:Sesquiterpene
3121:
3115:
3112:
3110:
3107:
3105:
3102:
3100:
3097:
3095:
3092:
3090:
3087:
3085:
3082:
3080:
3077:
3076:
3074:
3068:
3065:
3061:
3051:
3048:
3046:
3043:
3041:
3038:
3036:
3033:
3031:
3028:
3026:
3023:
3022:
3020:
3016:
3010:
3007:
3006:
3004:
2998:
2992:
2989:
2988:
2986:
2980:
2969:
2966:
2959:
2956:
2949:
2946:
2939:
2936:
2929:
2926:
2919:
2916:
2909:
2906:
2899:
2896:
2889:
2886:
2879:
2876:
2869:
2866:
2859:
2856:
2849:
2846:
2845:
2843:
2832:
2829:
2827:
2823:
2817:
2814:
2812:
2809:
2807:
2804:
2802:
2801:Oleyl alcohol
2799:
2797:
2794:
2792:
2789:
2787:
2784:
2782:
2779:
2778:
2776:
2774:
2766:
2760:
2757:
2755:
2752:
2750:
2747:
2745:
2742:
2740:
2737:
2735:
2732:
2730:
2727:
2725:
2722:
2721:
2719:
2717:
2711:
2705:
2702:
2700:
2697:
2695:
2692:
2691:
2689:
2687:
2683:
2677:
2674:
2672:
2669:
2667:
2664:
2662:
2659:
2657:
2654:
2652:
2649:
2647:
2644:
2642:
2639:
2638:
2636:
2634:
2633:Amyl alcohols
2630:
2615:
2612:
2605:
2601:
2598:
2591:
2588:
2581:
2577:
2574:
2567:
2563:
2560:
2553:
2550:
2548:
2545:
2544:
2542:
2540:
2536:
2530:
2527:
2526:
2524:
2520:
2514:
2511:
2509:
2506:
2505:
2503:
2499:
2488:
2487:Cetyl alcohol
2485:
2478:
2475:
2468:
2465:
2458:
2455:
2448:
2445:
2438:
2435:
2434:
2432:
2428:
2425:
2421:
2415:
2412:
2410:
2407:
2405:
2403:
2399:
2397:
2396:-Amyl alcohol
2395:
2391:
2389:
2387:
2382:
2380:
2377:
2375:
2374:Ethchlorvynol
2372:
2370:
2367:
2365:
2362:
2360:
2357:
2355:
2352:
2350:
2347:
2345:
2342:
2341:
2339:
2337:alcohols (3°)
2333:
2328:
2325:
2323:
2320:
2318:
2315:
2313:
2310:
2308:
2305:
2303:
2302:Cyclopropanol
2300:
2298:
2297:Cyclopentanol
2295:
2293:
2290:
2288:
2285:
2283:
2280:
2278:
2275:
2273:
2270:
2268:
2265:
2263:
2260:
2258:
2255:
2253:
2250:
2248:
2245:
2243:
2240:
2238:
2235:
2233:
2230:
2228:
2226:alcohols (2°)
2222:
2216:
2213:
2211:
2208:
2206:
2203:
2201:
2198:
2196:
2193:
2191:
2188:
2186:
2183:
2181:
2178:
2176:
2173:
2171:
2168:
2166:
2163:
2161:
2158:
2156:
2153:
2151:
2148:
2146:
2143:
2141:
2138:
2136:
2135:Allyl alcohol
2133:
2131:
2128:
2127:
2118:
2115:
2113:
2110:
2108:
2105:
2103:
2100:
2098:
2095:
2093:
2090:
2088:
2085:
2083:
2080:
2078:
2075:
2073:
2070:
2069:
2067:
2052:
2046:
2043:
2041:
2038:
2036:
2033:
2031:
2028:
2026:
2023:
2020:
2017:
2015:
2012:
2009:
2006:
2004:
2001:
1998:
1995:
1994:
1992:
1977:
1971:
1970:1-Nonacosanol
1968:
1965:
1964:1-Octacosanol
1962:
1960:
1957:
1954:
1953:1-Hexacosanol
1951:
1949:
1946:
1943:
1940:
1938:
1935:
1932:
1929:
1927:
1924:
1921:
1918:
1917:
1915:
1900:
1894:
1893:1-Nonadecanol
1891:
1888:
1887:1-Octadecanol
1885:
1883:
1880:
1877:
1876:1-Hexadecanol
1874:
1872:
1869:
1866:
1863:
1861:
1858:
1855:
1852:
1849:
1846:
1843:
1840:
1839:
1837:
1822:
1815:
1812:
1809:
1806:
1804:
1801:
1799:
1796:
1794:
1791:
1789:
1786:
1784:
1781:
1779:
1776:
1774:
1771:
1770:
1768:
1753:
1747:
1745:
1741:
1739:
1736:
1734:
1731:
1730:
1728:
1726:
1722:
1716:
1713:
1711:
1708:
1706:
1704:
1700:
1698:
1696:
1692:
1688:
1686:
1683:
1681:
1678:
1676:
1673:
1671:
1668:
1666:
1663:
1661:
1658:
1656:
1653:
1651:
1648:
1646:
1643:
1641:
1638:
1636:
1633:
1631:
1628:
1626:
1623:
1621:
1618:
1616:
1613:
1611:
1608:
1606:
1603:
1602:
1600:
1598:
1594:
1588:
1585:
1583:
1580:
1578:
1575:
1573:
1570:
1568:
1567:Aminomethanol
1565:
1563:
1560:
1559:
1557:
1555:
1551:
1548:
1545:
1539:
1529:
1526:
1524:
1521:
1520:
1518:
1516:
1512:
1504:
1501:
1500:
1498:
1496:
1493:
1491:
1490:Ethchlorvynol
1488:
1487:
1485:
1483:
1479:
1473:
1470:
1468:
1466:
1462:
1460:
1459:-Amyl alcohol
1458:
1454:
1452:
1449:
1447:
1444:
1442:
1439:
1437:
1434:
1432:
1429:
1427:
1424:
1423:
1421:
1419:
1413:
1410:
1406:
1402:
1395:
1390:
1388:
1383:
1381:
1376:
1375:
1372:
1353:
1347:
1345:
1336:
1332:
1328:
1324:
1320:
1316:
1309:
1301:
1295:
1291:
1290:
1282:
1274:
1268:
1264:
1263:
1255:
1247:
1246:
1238:
1230:
1226:
1221:
1216:
1211:
1206:
1202:
1198:
1194:
1187:
1179:
1173:
1169:
1168:
1161:
1153:
1147:
1143:
1142:
1134:
1127:
1121:
1114:
1108:
1100:
1096:
1092:
1088:
1084:
1080:
1077:(5): 482–90.
1076:
1072:
1064:
1062:
1053:
1049:
1045:
1041:
1037:
1033:
1026:
1024:
1015:
1011:
1007:
1003:
999:
995:
988:
980:
974:
970:
966:
962:
955:
953:
951:
949:
944:
936:
933:
929:
925:
915:
913:
909:
905:
901:
900:blood glucose
897:
887:
885:
881:
877:
873:
869:
865:
861:
856:
855:when heated.
854:
850:
845:
843:
839:
835:
821:
817:
813:
809:
805:
804:Carbohydrates
801:
797:
793:
789:
786:
783:
780:
777:
774:
772:
769:
768:
764:
761:
758:
755:
752:
749:
747:
744:
743:
739:
736:
733:
730:
727:
724:
722:
719:
718:
714:
711:
708:
705:
702:
699:
697:
694:
693:
689:
686:
683:
680:
677:
674:
672:
669:
668:
664:
661:
658:
655:
652:
649:
647:
644:
643:
639:
636:
633:
630:
627:
624:
619:
614:
613:
609:
606:
603:
600:
597:
594:
592:
589:
588:
584:
581:
578:
575:
572:
569:
567:
564:
563:
559:
556:
553:
550:
547:
544:
542:
539:
538:
534:
531:
529:
526:
523:
520:
517:
514:
511:
510:
504:
502:
498:
488:
486:
482:
478:
474:
473:disaccharides
464:
463:
456:
453:
450:
447:
444:
441:
438:
435:
432:
429:
426:
423:
420:
417:
414:
411:
408:
405:
402:
399:
396:
393:
390:
387:
384:
381:
378:
375:
372:
369:
366:
363:
360:
357:
354:
351:
348:
347:
340:
338:
334:
329:
327:
317:
315:
311:
307:
281:
280:
279:
277:
273:
272:hydrogenation
269:
260:
258:
250:
249:
248:hydrogenation
244:
236:
232:
228:
227:
221:
213:
212:hemicellulose
209:
205:
201:
191:
189:
185:
181:
177:
173:
161:
147:
129:
112:
110:
106:
102:
98:
93:
91:
83:
82:hydrogenating
75:
71:
67:
63:
59:
55:
51:
47:
44:(also called
43:
36:
32:
19:
3315:Substitution
3308:Preparations
3291:
3257:Stigmasterol
3252:β-Sitosterol
3050:Polyglycitol
3040:Maltotriitol
3000:Cyclic sugar
2825:
2768:Branched and
2676:Pentan-3-ol
2671:Pentan-2-ol
2666:Pentan-1-ol
2538:
2401:
2393:
2385:
2292:Cyclohexanol
1944:(lignoceryl)
1937:1-Tricosanol
1860:1-Tridecanol
1816:(pelargonic)
1743:
1702:
1694:
1690:
1685:Ethanolamine
1464:
1456:
1356:. Retrieved
1318:
1314:
1308:
1288:
1281:
1261:
1254:
1244:
1237:
1200:
1196:
1186:
1166:
1160:
1140:
1133:
1125:
1120:
1112:
1107:
1074:
1070:
1035:
1031:
997:
993:
987:
960:
921:
918:Side effects
893:
857:
846:
831:
819:
818:, are high.
802:is 100%. =
795:
494:
481:hydrogenated
470:
457:Polyglycitol
330:
323:
310:fermentation
304:
276:Raney nickel
266:
256:
246:
242:
230:
224:
197:
159:
145:
127:
118:
94:
64:, typically
57:
53:
50:polyalcohols
49:
45:
41:
40:
3373:Protonation
3290:Nonafluoro-
3237:Cholesterol
3214:Trialcohols
3084:Citronellol
3070:Monoterpene
2982:Deoxy sugar
2770:unsaturated
2457:Isopropanol
2384:Nonafluoro-
2312:Isopropanol
1931:1-Docosanol
1922:(arachidyl)
1854:1-Dodecanol
1848:1-Undecanol
1203:: 5967907.
868:crystalline
864:chewing gum
849:tooth decay
838:aftertastes
834:food energy
820:References:
519:Food energy
497:food energy
448:(12-carbon)
442:(12-carbon)
436:(12-carbon)
333:blood sugar
326:tooth decay
3462:Categories
3334:Hydrolysis
3319:haloalkane
3247:Lanosterol
3242:Ergosterol
3178:Dialcohols
3147:Patchoulol
2948:Galactitol
2878:Erythritol
2754:Tridecanol
2576:Erythritol
2477:1-Pentanol
2287:3-Pentanol
2282:2-Pentanol
2252:3-Heptanol
2247:2-Heptanol
2205:Tryptophol
2010:(lacceryl)
1920:1-Icosanol
1867:(myristyl)
1850:(hendecyl)
1803:1-Heptanol
1793:1-Pentanol
1783:1-Propanol
1738:Isobutanol
1472:Tryptophol
1446:Isobutanol
1426:1-Propanol
1358:January 6,
1197:Int J Dent
1071:Caries Res
939:References
932:flatulence
912:erythritol
860:hard candy
853:caramelize
842:sweeteners
796:Footnotes:
566:Erythritol
430:(7-carbon)
418:(6-carbon)
412:(6-carbon)
406:(6-carbon)
404:Galactitol
400:(6-carbon)
394:(6-carbon)
388:(5-carbon)
382:(5-carbon)
376:(5-carbon)
370:(4-carbon)
364:(4-carbon)
362:Erythritol
358:(3-carbon)
352:(2-carbon)
306:Erythritol
301:Erythritol
194:Production
188:isosorbide
35:Erythritol
3361:Reactions
3343:Hydration
3156:Diterpene
3142:Nerolidol
3132:Bisabolol
3114:Terpineol
2968:Volemitol
2759:Undecanol
2713:Saturated
2614:Volemitol
2467:1-Butanol
2277:2-Octanol
2272:2-Nonanol
2262:3-Hexanol
2257:2-Hexanol
2237:2-Butanol
2224:Secondary
2056:saturated
1981:saturated
1933:(behenyl)
1904:saturated
1889:(stearyl)
1842:1-Decanol
1826:saturated
1814:1-Nonanol
1808:1-Octanol
1798:1-Hexanol
1788:1-Butanol
1757:saturated
904:diabetics
762:0.17–0.24
582:0.66–1.0+
428:Volemitol
208:cellulose
115:Structure
58:glycitols
3447:Category
3221:Glycerol
3158:alcohols
3137:Farnesol
3125:alcohols
3109:Rhodinol
3094:Linalool
3089:Geraniol
3072:alcohols
3030:Lactitol
3025:Maltitol
3009:Inositol
3002:alcohols
2984:alcohols
2938:Sorbitol
2928:Mannitol
2898:Arabitol
2888:Threitol
2868:Glycerol
2604:Sorbitol
2600:Mannitol
2580:Threitol
2562:Glycerol
2529:Glycerol
2437:Methanol
2335:Tertiary
2021:(geddyl)
1856:(lauryl)
1844:(capric)
1810:(capryl)
1773:Methanol
1746:-Butanol
1554:Methanol
1544:alcohols
1528:Methanol
1401:Alcohols
1335:98559442
1229:27840639
1091:24852946
1014:22374680
928:diarrhea
924:bloating
876:maltitol
872:lactitol
816:fructose
808:fructose
787:0.3–0.42
746:Sorbitol
721:Mannitol
696:Maltitol
671:Lactitol
591:Glycerol
541:Arabitol
521:(kcal/g)
446:Lactitol
440:Maltitol
422:Inositol
398:Sorbitol
392:Mannitol
374:Arabitol
368:Threitol
356:Glycerol
268:Mannitol
243:polymers
235:cleavage
184:sorbitan
172:pentoses
109:sorbitol
74:hydroxyl
54:alditols
3338:epoxide
3230:Sterols
3099:Menthol
3079:Borneol
3035:Isomalt
2991:Fucitol
2918:Xylitol
2908:Ribitol
2749:Octanol
2744:Nonanol
2729:Decanol
2590:Xylitol
2447:Ethanol
1955:(ceryl)
1778:Ethanol
1725:Butanol
1680:Ethanol
1597:Ethanol
1542:Primary
1503:Ethanol
1436:Ethanol
1220:5093271
1099:5442856
1052:8069881
812:Glucose
800:Sucrose
771:Xylitol
646:Isomalt
434:Isomalt
410:Fucitol
386:Ribitol
380:Xylitol
314:sucrose
176:hexoses
105:Xylitol
97:sucrose
90:polyols
66:derived
3347:alkene
3165:Phytol
2958:Iditol
2190:Prenol
1333:
1296:
1269:
1227:
1217:
1174:
1148:
1097:
1089:
1050:
1012:
975:
878:. The
765:Minor
740:Minor
715:Minor
690:Minor
460:
416:Iditol
291:→ HOCH
204:starch
164:C(O)CH
157:(CHOH)
143:(CHOH)
125:(CHOH)
76:group
70:sugars
60:) are
3104:Nerol
1331:S2CID
1095:S2CID
790:None
784:12–13
750:40–70
725:40–70
709:35–52
675:30–40
650:45–65
625:40–90
585:None
570:60–80
471:Both
86:(−OH)
78:(−OH)
68:from
3292:tert
2402:tert
2394:tert
2386:tert
1546:(1°)
1465:tert
1457:tert
1360:2018
1294:ISBN
1267:ISBN
1225:PMID
1201:2016
1172:ISBN
1146:ISBN
1087:PMID
1048:PMID
1010:PMID
973:ISBN
930:and
874:and
687:0.34
617:HSHs
573:0.21
512:Name
475:and
283:HOCH
233:the
231:i.e.
210:and
153:HOCH
139:HOCH
121:HOCH
107:and
3412:of
3345:of
3336:of
3317:of
2838:— C
2062:— C
1987:— C
1910:— C
1832:— C
1763:— C
1323:doi
1215:PMC
1205:doi
1079:doi
1040:doi
1002:doi
965:doi
862:or
778:2.4
775:100
753:2.6
737:0.3
728:1.6
712:0.3
703:2.1
684:5–6
678:2.0
662:0.3
659:2–9
653:2.0
628:3.0
601:108
598:4.3
576:5.3
551:5.0
548:0.2
253:C=O
251:of
239:C−O
237:of
190:).
151:or
149:CHO
56:or
3464::
2970:(C
2960:(C
2950:(C
2940:(C
2930:(C
2920:(C
2910:(C
2900:(C
2890:(C
2880:(C
2870:(C
2860:(C
2850:(C
2616:(C
2606:(C
2602:,
2592:(C
2582:(C
2578:,
2568:(C
2564:,
2554:(C
2491:16
2489:(C
2479:(C
2469:(C
2459:(C
2449:(C
2439:(C
2064:49
2060:40
1989:39
1985:30
1912:29
1908:20
1834:19
1830:10
1343:^
1329:.
1319:47
1317:.
1223:.
1213:.
1199:.
1195:.
1093:.
1085:.
1075:48
1073:.
1060:^
1046:.
1036:28
1034:.
1022:^
1008:.
998:51
996:.
971:.
947:^
926:,
886:.
844:.
798:=
781:60
756:65
731:40
706:53
700:90
681:50
665:?
656:50
640:?
634:35
631:75
610:?
595:60
560:?
545:70
339:.
316:.
259:.
229:,
206:,
168:OH
162:−1
135:OH
131:CH
92:.
52:,
48:,
2974:)
2972:7
2964:)
2962:6
2954:)
2952:6
2944:)
2942:6
2934:)
2932:6
2924:)
2922:5
2914:)
2912:5
2904:)
2902:5
2894:)
2892:4
2884:)
2882:4
2874:)
2872:3
2864:)
2862:2
2854:)
2852:1
2840:7
2836:1
2834:C
2620:)
2618:7
2610:)
2608:6
2596:)
2594:5
2586:)
2584:4
2572:)
2570:3
2558:)
2556:2
2493:)
2483:)
2481:5
2473:)
2471:4
2463:)
2461:3
2453:)
2451:2
2443:)
2441:1
2058:C
1983:C
1906:C
1828:C
1765:9
1761:1
1759:C
1744:n
1703:N
1695:N
1693:,
1691:N
1393:e
1386:t
1379:v
1362:.
1337:.
1325::
1302:.
1275:.
1231:.
1207::
1180:.
1154:.
1101:.
1081::
1054:.
1042::
1016:.
1004::
981:.
967::
759:9
734:0
637:?
607:?
604:3
579:0
557:?
554:?
293:2
289:2
285:2
219:2
217:H
166:2
160:n
155:2
146:n
141:2
133:2
128:n
123:2
20:)
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