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36:
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Alicyclic musks, otherwise known as cycloalkyl ester or linear musks, are a relatively novel class of musk compounds. The first compound of this class was introduced 1975 with
Cyclomusk, though similar structures were noted earlier in citronellyl oxalate and Rosamusk. Alicyclic musks are dramatically
415:
was able to synthesize this compound in very small quantities. Despite this discovery and the discovery of other pathways for synthesis of macrocyclic musks, compounds of this class were not commercially produced and commonly utilized until the late 1990s due to difficulties in their synthesis and
399:
A class of artificial musk consisting of a single ring composed of more than 6 carbons (often 10–15). Of all artificial musks, these most resemble the primary odoriferous compound from Tonkin musk in its "large ringed" structure. While the macrocyclic musks extracted from plants consists of large
353:
functional group from nitro-musks due to their photochemical reactivity and their instability in alkaline media. This was shown to be possible through the discovery of ambroxide, a non-nitro aromatic musk, which promoted research in the development of nitro-free musks. This led to the eventual
358:
without initial knowledge of its chemical structure (elucidated 4 years later). While poorer in smell strength, the performance and stability of this compound class in harsh detergents led to its common use, which spurred further development of other polycyclic musks including
919:
Tumová, Jitka; Šauer, Pavel; Golovko, Oksana; Koba Ucun, Olga; Grabic, Roman; Máchová, Jana; Kocour
Kroupová, Hana (2019). "Effect of polycyclic musk compounds on aquatic organisms: A critical literature review supplemented by own data".
688:
different in structure than previous musks (aromatic, polycyclic, macrocyclic) in that they are modified alkyl esters. Although they were discovered prior to 1980, it was only in 1990 with the discovery and introduction of
Helvetolide at
708:, which are found in perfume formulas, can lead to allergic reactions, hormone disruption and it has been suggested that exposure to perfumes and/or synthetic fragrances may be linked to the development of
963:
Sealey, L.A.; Hughes, B.W.; Sriskanda, A.N.; Guest, J.R.; Gibson, A.D.; Johnson-Williams, L.; Pace, D.G.; Bagasra, O. (2016). "Environmental factors in the development of autism spectrum disorders".
692:
that a compound of this class was produced at a commercial scale. Romandolide, a more ambrette and less fruity alicyclic musk compared to
Helvetolide, was introduced ten years later.
700:
Synthetic musks are lipophilic compounds and tend to deposit and persist in fat tissues. Nitromusks and polycyclic musks – having been used for 100 years – have low
617:
605:
194:
in civet. Muscone and civetone are macrocyclic ketones. Other structurally different but functionally similar compounds also came to be known as musks.
215:
519:
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222:, and nitrating the product. It was discovered accidentally as a result of Baur's attempts at producing a more effective form of
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100:
72:
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79:
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155:). Synthetic musks have a clean, smooth and sweet scent lacking the fecal notes of animal musks. They are used as
53:
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57:
17:
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68:
1014:
802:
Charles (Ed.), Sell; Charles Sell (2005). "Chapter 4. Ingredients for the Modern
Perfumery Industry".
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Although muscone, the primary macrocyclic compound of musk was long known, it was only in 1926 that
186:
Synthetic musks in a narrower sense are chemicals modeled after the main odorants in animal musk:
46:
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The creation of this class of musks was largely prompted through the need for eliminating the
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219:
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Philip Kraft (2004). "Chapter 7. Aroma
Chemicals IV: Musks". In Rowe, David J. (ed.).
226:(TNT). It appears that the odour depends upon the symmetry of the three nitro groups.
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of many perfume formulas. Most musk fragrance used in perfumery today is synthetic.
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937:
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701:
665:
635:(-)-(6S,7S)-3,5,5,6,7,8,8-heptamethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde
876:
Eh, Marcus (2004). "New
Alicyclic Musks: The Fourth Generation of Musk Odorants".
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1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8,-tetramethyl-2-naphthyl)ethan-1-one
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and accumulate in the environment. Chemicals such as musk ketone and
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An artificial musk was obtained by Albert Baur in 1888 by condensing
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355:
191:
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4,6,6,7,8,8-Hexamethyl-1,3,4,6,7,8-hexahydrocyclopentabenzopyrane
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discovery of phantolide, so named due to its commercialization by
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1,2,3,5,6,7-Hexahydro-1,1,2,3,3-pentamethyl-4H-inden-4-one
176:
144:
962:
801:
333:
806:(2nd ed.). Royal Society of Chemistry Publishing.
830:Kraft, Philip (2004). "'Brain Aided' Musk Design".
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Chemistry and
Technology of Flavours and Fragrances
60:. Unsourced material may be challenged and removed.
695:
996:
647:6-Acetyl-1,1,2,4,4,7-hexamethyltetraline (AHTN)
244:-Butyl-2',6'-dimethyl-3',5'-dinitroacetophenone)
589:(10Z)-13-methyl-1-oxacyclopentadec-10-en-2-one
300:5-Acetyl-1,1,2,6-tetramethyl-3-isopropylindane
367:3a,6,6,9a-Tetramethyldodecahydronaphtho-furan
316:Cashmeran, not a true musk but with musk odor
825:
823:
776:
404:, all animal derived macrocyclic musks are
237:-Butyl-3,5-dimethyl-2,4,6-trinitrobenzene)
820:
281:4-Acetyl-1,1-dimethyl-6-tert-butylindane
120:Learn how and when to remove this message
678:
488:
390:
340:
332:
259:
201:
772:
770:
570:α,ω-Tridecanedioic acid ethylene ester
484:
14:
997:
558:α,ω-Dodecanedioic acid ethylene ester
386:
269:6-Acetyl-1,1,2,3,3,5-hexamethylindane
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255:
871:
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767:
626:
251:-butyl-3-methoxy-2,6-dinitrotoluene)
58:adding citations to reliable sources
29:
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452:3-Methylcyclopentadec-4/5-en-1-one
24:
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674:
25:
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866:
922:Science of the Total Environment
613:14-Methylpentadecano-15-lactone
328:
34:
942:10.1016/j.scitotenv.2018.10.028
696:Environmental and health issues
527:Oxacyclohexadec-12/13-en-2-one
420:(R)-3-Methylcyclopentadecanone
45:needs additional citations for
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912:
752:
737:
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197:
13:
1:
715:
977:10.1016/j.envint.2015.12.021
878:Chemistry & Biodiversity
832:Chemistry & Biodiversity
430:(Z)-9-Cycloheptadecen-1-one
7:
804:The Chemistry of Fragrances
416:consequently higher price.
10:
1031:
965:Environment International
546:12-Oxa-16-hexadecanolide
135:are a class of synthetic
710:autism spectrum disorder
139:to emulate the scent of
27:Type of synthetic scents
604:Ambrettolide (found in
464:5-Cyclohexadecen-1-one
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844:10.1002/cbdv.200490150
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659:Haarmann & Reimer
601:ω-6-Hexadecenlactone
580:Ethylene Brassylate (
539:Haarmann & Reimer
506:Haarmann & Reimer
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344:
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274:Haarmann & Reimer
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205:
616:Muscolide (found in
502:Cyclopentadecanolide
493:Cyclopentadecanolide
485:Macrocyclic lactones
54:improve this article
1010:Perfume ingredients
934:2019ScTEn.651.2235T
498:15-Pentadecanolide
440:Cyclopentadecanone
387:Macrocyclic ketones
218:in the presence of
1015:Chemical synthesis
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256:(Hydrated) indanes
220:aluminium chloride
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190:in deer musk, and
884:(12): 1975–1984.
838:(12): 1957–1974.
813:978-0-85404-824-3
706:diethyl phthalate
627:Hydronaphthalenes
618:Angelica seed oil
606:Ambrette seed oil
247:Musk ambrette (4-
143:and other animal
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16:(Redirected from
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702:biodegradability
666:Bush Boake Allen
240:Musk ketone (4'-
216:isobutyl bromide
179:, supplying the
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137:aroma compounds
133:Synthetic musks
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638:Vulcanolide (
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592:Nirvanolide (
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65:Find sources:
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43:This article
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18:Musk ambrette
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530:Habanolide (
511:Exaltolide (
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303:Traseolide (
272:Phantolide (
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52:Please help
47:verification
44:
971:: 288–298.
683:Helvetolide
664:Tetralide (
537:Globalide (
518:Pentalide (
474:Ambretone (
455:Muscenone (
291:Crysolide (
231:Musk xylene
206:Musk xylene
198:Nitro musks
999:Categories
716:References
657:Tonalide (
650:Fixolide (
561:Arova 16 (
549:Musk R 1 (
467:TM II SP (
443:Exaltone (
374:Galaxolide
361:Galaxolide
345:Galaxolide
169:detergents
157:flavorings
80:newspapers
729:CID 62329
690:Firmenich
640:Firmenich
532:Firmenich
513:Firmenich
457:Firmenich
445:Firmenich
337:Ambroxide
264:Cashmeran
181:base note
165:cosmetics
161:fixatives
149:castoreum
141:deer musk
1005:Perfumes
985:26826339
950:53019067
906:31505456
898:17191833
860:21645119
852:17191832
759:CID 6753
744:CID 6669
575:Takasago
573:Musk T (
476:Takasago
434:Civetone
402:lactones
356:Givaudan
192:civetone
173:perfumes
110:May 2020
930:Bibcode
763:PubChem
748:PubChem
733:PubChem
582:Degussa
563:Degussa
424:Muscone
406:ketones
400:ringed
395:Muscone
212:toluene
188:muscone
94:scholar
983:
948:
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946:S2CID
902:S2CID
856:S2CID
761:from
746:from
731:from
551:Quest
351:nitro
305:Quest
214:with
177:foods
153:civet
145:musks
101:JSTOR
87:books
981:PMID
894:PMID
848:PMID
808:ISBN
783:ISBN
249:tert
242:tert
235:tert
175:and
159:and
151:and
73:news
973:doi
938:doi
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886:doi
840:doi
378:IFF
320:IFF
286:IFF
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163:in
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