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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 almost insoluble in water and [[glycerin]], but very soluble in [[ethanol]]. 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 almost insoluble in water and [[glycerin]], but very soluble in [[ethanol]]. 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 name="JAOCS">J Am Oil Chem Soc (2010) 87;1-7.</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|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>

α-bisabolol has recently been shown to induce [[apoptosis]] in models of [[leukemia]].<ref>{{cite journal|last=Cavalieri|first=E |author2=Rigo, A |author3=Bonifacio, M |author4=Carcereri de Prati, A |author5=Guardalben, E |author6=Bergamini, C |author7=Fato, R |author8=Pizzolo, G |author9=Suzuki, H |author10=Vinante, F |title=Pro-apoptotic activity of α-bisabolol in preclinical models of primary human acute leukemia cells.|journal=Journal of translational medicine|date=Apr 21, 2011|volume=9|pages=45|pmid=21510902|doi=10.1186/1479-5876-9-45|pmc=3112094}}</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.
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.

Revision as of 08:45, 13 January 2017

α-(−)-Bisabolol
α-(−)-Bisabolol
Names
IUPAC name
6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-ol
Other names
Levomenol
Identifiers
3D model (JSmol)
5733954
ChEMBL
ChemSpider
ECHA InfoCard 100.041.279 Edit this at Wikidata
UNII
  • 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
  • O[C@@](C)(CC\C=C(/C)C)[C@@H]1C/C=C(/C)CC1
Properties
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).

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 almost insoluble in water and glycerin, but very soluble in ethanol. 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.[3]

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.

β-Bisabolol

References

  1. ^ Rohstoff-Lexikon Bisabolol Archived February 20, 2008, at the Wayback Machine
  2. ^ Bisabolol (in english) Archived October 10, 2007, at the Wayback Machine
  3. ^ Kamatou, Guy P. P.; Viljoen, Alvaro M. (2010). "A Review of the Application and Pharmacological Properties of α-Bisabolol and α-Bisabolol-Rich Oils" (PDF). Journal of the American Oil Chemists' Society. 87 (1): 1–7. doi:10.1007/s11746-009-1483-3.
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