Bisabolol: Difference between revisions

α-(−)-Bisabolol
Names
	IUPAC name 6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-ol
	Other names Levomenol
Identifiers
CAS Number	23089-26-1;
3D model (JSmol)	Interactive image;
Beilstein Reference	5733954
ChEMBL	ChEMBL1096927;
ChemSpider	390796;
ECHA InfoCard	100.041.279
PubChem CID	10586;
UNII	24WE03BX2T;
CompTox Dashboard (EPA)	DTXSID4042094 ;
	InChI InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3 Key: RGZSQWQPBWRIAQ-UHFFFAOYSA-N; InChI=1/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m1/s1 Key: RGZSQWQPBWRIAQ-CABCVRREBV; InChI=1/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m1/s1 Key: RGZSQWQPBWRIAQ-CABCVRREBV;
	SMILES O[C@@](C)(CC\C=C(/C)C)[C@@H]1C/C=C(/C)CC1;
Properties
Chemical formula	C15H26O
Molar mass	222.372 g·mol−1
Density	0.92 g cm−3
Boiling point	153 °C (307 °F; 426 K) at 12 mmHg
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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Revision as of 19:29, 11 October 2020

Bisabolol, or more formally α-(−)-bisabolol or also known as levomenol,^[1] is a natural monocyclic sesquiterpene alcohol. It is a colorless viscous oil that is the primary constituent of the essential oil from German chamomile (Matricaria recutita) and Myoporum crassifolium.^[2] It is poorly soluble in water and glycerin, but soluble in ethanol.^[3] The enantiomer, α-(+)-bisabolol, is also found naturally but is rare. Synthetic bisabolol is usually a racemic mixture of the two, α-(±)-bisabolol.

Bisabolol has a weak sweet floral aroma and is used in various fragrances. It has also been used for hundreds of years in cosmetics because of its perceived skin healing properties. Bisabolol is known to have anti-irritant, anti-inflammatory, and anti-microbial properties. Bisabolol is also demonstrated to enhance the percutaneous absorption of certain molecules.^[4]

A structurally related compound known as β-bisabolol (CAS registry number [15352-77-9]) differs only in the position of the tertiary alcohol functional group.

References

^ Rohstoff-Lexikon Bisabolol Archived February 20, 2008, at the Wayback Machine
^ Bisabolol (in english) Archived October 10, 2007, at the Wayback Machine
^ "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2005. doi:10.1002/14356007.a26_205. ISBN 3527306730. {{cite encyclopedia}}: Unknown parameter |authors= ignored (help)
^ Kamatou, Guy P. P.; Viljoen, Alvaro M. (2010). "A Review of the Application and Pharmacological Properties of α-Bisabolol and α-Bisabolol-Rich Oils". Journal of the American Oil Chemists' Society. 87 (1): 1–7. doi:10.1007/s11746-009-1483-3. S2CID 95169851.

[1] Rohstoff-Lexikon Bisabolol Archived February 20, 2008, at the Wayback Machine

[2] Bisabolol (in english) Archived October 10, 2007, at the Wayback Machine

[UllmannEgg-3] "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2005. doi:10.1002/14356007.a26_205. ISBN 3527306730. {{cite encyclopedia}}: Unknown parameter |authors= ignored (help)

[4] Kamatou, Guy P. P.; Viljoen, Alvaro M. (2010). "A Review of the Application and Pharmacological Properties of α-Bisabolol and α-Bisabolol-Rich Oils". Journal of the American Oil Chemists' Society. 87 (1): 1–7. doi:10.1007/s11746-009-1483-3. S2CID 95169851.

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-'''Bisabolol''', or more formally α-(−)-bisabolol or also known as levomenol,<ref>[http://www.omikron-online.de/naturhaus/angebote/info/bisabolo.htm Rohstoff-Lexikon Bisabolol<!-- Bot generated title -->] {{webarchive |url=https://web.archive.org/web/20080220222428/http://www.omikron-online.de/naturhaus/angebote/info/bisabolo.htm |date=February 20, 2008 }}</ref> is a natural monocyclic [[sesquiterpene]] alcohol.   It is a colorless viscous oil that is the primary constituent of the [[essential oil]] from [[German chamomile]] (''[[Matricaria recutita]]'') and ''[[Myoporum crassifolium]]''.<ref>[http://www.omikron-online.de/naturhaus/angebote/info/bisab.htm Bisabolol (in english)<!-- Bot generated title -->] {{webarchive |url=https://web.archive.org/web/20071010110347/http://www.omikron-online.de/naturhaus/angebote/info/bisab.htm |date=October 10, 2007 }}</ref>  It is poorly soluble in water and [[glycerin]], but soluble in [[ethanol]].<ref name=UllmannEgg>{{cite encyclopedia|authors=M. Eggersdorfer|title=Terpenes|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a26_205}}</ref>   The [[enantiomer]], α-(+)-bisabolol, is also found naturally but is rare.  Synthetic bisabolol is usually a [[racemic]] mixture of the two, α-(±)-bisabolol.
+'''Bisabolol''', or more formally α-(−)-bisabolol or also known as levomenol,<ref>[http://www.omikron-online.de/naturhaus/angebote/info/bisabolo.htm Rohstoff-Lexikon Bisabolol<!-- Bot generated title -->] {{webarchive |url=https://web.archive.org/web/20080220222428/http://www.omikron-online.de/naturhaus/angebote/info/bisabolo.htm |date=February 20, 2008 }}</ref> is a natural monocyclic [[sesquiterpene]] alcohol.   It is a colorless viscous oil that is the primary constituent of the [[essential oil]] from [[German chamomile]] (''[[Matricaria recutita]]'') and ''[[Myoporum crassifolium]]''.<ref>[http://www.omikron-online.de/naturhaus/angebote/info/bisab.htm Bisabolol (in english)<!-- Bot generated title -->] {{webarchive |url=https://web.archive.org/web/20071010110347/http://www.omikron-online.de/naturhaus/angebote/info/bisab.htm |date=October 10, 2007 }}</ref>  It is poorly soluble in water and [[glycerin]], but soluble in [[ethanol]].<ref name=UllmannEgg>{{cite encyclopedia|authors=M. Eggersdorfer|title=Terpenes|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a26_205|isbn=3527306730}}</ref>   The [[enantiomer]], α-(+)-bisabolol, is also found naturally but is rare.  Synthetic bisabolol is usually a [[racemic]] mixture of the two, α-(±)-bisabolol.
-Bisabolol has a weak sweet floral aroma and is used in various fragrances.  It has also been used for hundreds of years in cosmetics because of its perceived skin healing properties.  Bisabolol is known to have anti-irritant, anti-inflammatory, and anti-microbial properties. Bisabolol is also demonstrated to enhance the percutaneous absorption of certain molecules.<ref>{{cite journal|last1=Kamatou|first1=Guy P. P.|last2=Viljoen|first2=Alvaro M.|title=A Review of the Application and Pharmacological Properties of α-Bisabolol and α-Bisabolol-Rich Oils|journal=Journal of the American Oil Chemists' Society|date=2010|volume=87|issue=1|pages=1–7|doi=10.1007/s11746-009-1483-3|url=https://www.researchgate.net/profile/Guy_Paulin_Kamatou/publication/225389970_A_Review_of_the_Application_and_Pharmacological_Properties_of_a-Bisabolol_and_a-Bisabolol-Rich_Oils/links/56e9594a08ae47bc651c6cd0.pdf}}</ref>
+Bisabolol has a weak sweet floral aroma and is used in various fragrances.  It has also been used for hundreds of years in cosmetics because of its perceived skin healing properties.  Bisabolol is known to have anti-irritant, anti-inflammatory, and anti-microbial properties. Bisabolol is also demonstrated to enhance the percutaneous absorption of certain molecules.<ref>{{cite journal|last1=Kamatou|first1=Guy P. P.|last2=Viljoen|first2=Alvaro M.|title=A Review of the Application and Pharmacological Properties of α-Bisabolol and α-Bisabolol-Rich Oils|journal=Journal of the American Oil Chemists' Society|date=2010|volume=87|issue=1|pages=1–7|doi=10.1007/s11746-009-1483-3|s2cid=95169851|url=https://www.researchgate.net/publication/225389970}}</ref>
 A structurally related compound known as β-bisabolol ([[CAS registry number]] [15352-77-9]) differs only in the position of the tertiary alcohol functional group.