Quick Search
Bisabolol, or more formally α-(−)-bisabolol or also known as levomenol,[1] is a natural monocyclic sesquiterpene alcohol.
Bisabolol is a colorless viscous oil that is the primary constituent of the essential oil from German chamomile (Matricaria recutita) and Myoporum crassifolium.
High concentrations of Bisabolol can also be found in certain medicinal cannabis cultivars.
CAS: 515-69-5
MF: C15H26O
MW: 222.37
EINECS: 208-205-9
Synonyms
(R*, R*)-alpha, 4-Dimethyl-alpha-(4-methyl-3-pentyl)cyclohex-3-en-1-methanol;(R*,R*)-alpha-4-Dimethyl-alpha-(4-methyl-3-petenyl)-3-cyclohexene-1-methanol;α-bisabolol,6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol,dragosantol;3-Cyclohexene-1-methanol, .alpha.,4-dimethyl-.alpha.-(4-methyl-3-pentenyl)-, (.alpha.R,1R)-rel-;6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepteno;alpha-Bisabalol;alpha-bisabolool;Camilol
;alpha-Bisabolol;Bisabolol;515-69-5;(+)-alpha-Bisabolol;23178-88-3;(2R)-6-methyl-2-[(1R)--methylcyclohex-3-en-1-yl]hept-5-en-2-ol;D-alpha-Bisabolol;(+)-(1'R,2R)-alpha-Bisabolol;MFCD03846910;Dragosantol;Camilol;Anymol;(AlphaR,1R)-Alpha-Bisabolol;36HQN158VC;CHEMBL1171719;DTXSID5045964;Hydagen B;105S6I733Z;(2R)-6-Methyl-2-(4-methyl-3-cyclohexenyl)-5-heptene-2-ol;(R)-6-Methyl-2-((R)-4-methylcyclohex-3-en-1-yl)hept-5-en-2-ol;5-HEPTEN-2-OL, 6-METHYL-2-(4-METHYL-3-CYCLOHEXEN-1-YL)-;alpha,4-Dimethyl-alpha-(4-methyl-3-pentenyl)-3-cyclohexene-1-methanol;3-Cyclohexene-1-methanol, .alpha.,4-dimethyl-.alpha.-(4-methyl-3-pentenyl)-, (R*,R*)-;DTXCID3025964;rel-(R)-6-Methyl-2-((R)-4-methylcyclohex-3-en-1-yl)hept-5-en-2-ol;dl-.alpha.-Bisabolol;6-Methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol;BISABOLOL, ALPHA;CAS-515-69-5;BISABOLOL, .ALPHA.;RACEMIC ALFA-BISABOLOL;alpha-Bisabolol, (+)-;UNII-36HQN158VC;BISABOLA-1,12-DIEN-8-OL;UNII-105S6I733Z;alpha-Bisabolol (+)-form [MI];NCGC00095252-01;3-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-penten-1-yl)-, (alphaR,1R)-rel-;(+)-a-Bisabolol
;EINECS 208-205-9;EINECS 246-973-7;+/-alpha-Bisabolol;(+)-.alpha.-Bisabolol;BISABOLOL [WHO-DD];3-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-penten-1-yl)-, (alphaR,1R)-;D-.ALPHA.-BISABOLOL;SCHEMBL24988;(+)-6R,7R-alpha-Bisabolol
;.alpha.,4-Dimethyl-.alpha.-(4-methyl-3-pentenyl)-3-cyclohexene-1-methanol;.ALPHA.-BISABOLOL [MI];BISABOLOL, (+/-)-;(R*,R*)-.alpha.,4-Dimethyl-.alpha.-(4-methyl-3-pentenyl)-3-cyclohexene-1-methanol;(R*,R*)-.alpha.,4-Dimethyl-.alpha.-(4-methyl-3-pentenyl)cyclohex-3-ene-1-methanol;CHEBI:192031;ALPHA-BISABOLOL, (+-)-;3-Cyclohexene-1-methanol, .alpha.,4-dimethyl-.alpha.-(4-methyl-3-penten-1-yl)-, ;(.alpha.R,1R)-rel-;(+/-)-.ALPHA.-BISABOLOL;.ALPHA.-BISABOLOL, (+)-;Tox21_111490;BDBM50284328;s6136;AKOS015969722;Tox21_111490_1;.ALPHA.-BISABOLOL, (+/-)-;(R*,R*)-alpha,4-Dimethyl-alpha-(4-methyl-3-pentenyl)cyclohex-3-ene-1-methanol;NCGC00095252-05;25428-43-7;( inverted exclamation markA)-|A-Bisabolol;.ALPHA.-BISABOLOL (+)-FORM [MI];1ST158680;HY-121222;(+)-(1'R,2R)-.ALPHA.-BISABOLOL;CS-0081254;W-105877;(2R)-6-Methyl-2-[(1R)-4-methyl-3-cyclohexen-1-yl]-5-hepten-2-ol
;3-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-pentenyl)-
(R*,R*)-(1)-alpha,4-Dimethyl-alpha-(4-methyl-3-pentenyl)cyclohex-3-ene-1-methanol;3-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-pentenyl)-, (alphaR,1R)-rel-;3-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-pentenyl)-, (R*,R*)-
alpha,4-Dimethyl-alpha-(4-methyl-3-penten-1-yl)-(alphaR,1R)-3-Cyclohexene-1-methanol;3-CYCLOHEXENE-1-METHANOL, .ALPHA.,4-DIMETHYL-.ALPHA.-(4-METHYL- 3-PENTEN-1-YL)-, (.ALPHA.R,1R)-REL-;3-CYCLOHEXENE-1-METHANOL, .ALPHA.,4-DIMETHYL-.ALPHA.-(4-METHYL- 3-PENTENYL)-, (.THETA.,.THETA.)-(+/-)-;3-CYCLOHEXENE-1-METHANOL, .ALPHA.,4-DIMETHYL-.ALPHA.-(4-METHYL- 3-PENTENYL)-, (R*,R*)-;3-CYCLOHEXENE-1-METHANOL, .ALPHA.,4-DIMETHYL-.ALPHA.-(4-METHYL-3-PENTEN-1-YL)-, (.ALPHA.R,1R)-;3-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-pentenyl)-, (theta,theta)-(+/-)-
Bisabolol is poorly soluble in water and glycerine, but 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 is the terpenoid responsible for distinctive aroma of chamomile flowers, and when isolated, its scent has also has been likened to apples, sugar and honey.
Bisabolol has a weak sweet floral aroma and is used in various fragrances.
Bisabolol has also been used for hundreds of years in cosmetics because of its skin healing properties including reducing wrinkles, skin toughness and repairing sun-damaged skin, and more recently it has been compounded with tretinoin as a topical treatment for acne.
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 and has found use as a penetration enhancer: an agent used in topical formulations, increasing the substances propensity for absorption beneath the skin.
A structurally related compound known as β-bisabolol differs only in the position of the tertiary alcohol functional group.
(+)-alpha-Bisabolol is a sesquiterpenoid.
Bisabolol (also known as 'Alpha-bisabolol' or 'bisabol') is a naturally occurring compound that is derived from the Candeia Tree.
Bisabolol has a pleasant woody and floral aroma, which makes it a useful addition to fragrances.
This wonderful ingredient is extremely beneficial when used in skincare products.
Bisabolol has been shown to possess anti-inflammatory, anti-bacterial and skin healing properties.
Bisabolol can help soothe and moisturise the skin, whilst reducing dryness and restoring suppleness.
Bisabolol is a natural antioxidant.
Bisabolol can help protect your skin from pollution and free radicals and assist with repairing any damaged caused by these.
Bisabolol is a sesquiterpene lactone that is found in plants such as chamomile and rose. Bisabolol has been shown to have amoebicidal activity in vitro, as well as antiinflammatory activity.
Bisabolol has also been shown to have mitochondrial membrane potential-modulating effects and to inhibit the growth of human cancer cells.
Bisabolol can act intracellularly by inhibiting protein synthesis, which may lead to apoptosis.
Bisabolol also inhibits the production of pro-inflammatory cytokines, such as TNF-α and IL-1β, which are involved in tumorigenesis.
Bisabolol can also bind to polymyxin B and form a complex that is more effective than polymyxin B alone at killing bacteria.
Bisabolol is a well-known skin soothing agent.
Bisabolol comes in two different structural forms: alpha-bisabolol, derived from chamomile and other plants (although it can also be lab-created) vs. beta-bisabolol which is found in cotton and corn.
The alpha form is the one used in skin care products.
Bisabolol is commonly found in many personal care products, including moisturisers, cleansers, and serums.
Bisabolol often plays a bio-active skin-calming role thanks to its anti-inflammatory properties and shows up in many products designed for sensitive skin.
Beyond its soothing properties, research indicates bisabolol may offer some discoloration-fading capabilities.
The naturally sweet, slightly floral scent of bisabolol means Bisabolol is sometimes used in higher amounts to impart fragrance to a formula.
However, in lower amounts Bisabolol doesn’t impart much, if any, scent and its soothing compounds easily outweigh any risk of irritation.
Because bisabolol is typically derived from chamomile, and chamomile is a member of the ragweed family, it may be best to avoid Bisabolol if you have a confirmed allergy to ragweed.
Bisabolol Chemical Properties
Melting point: 25°C
Boiling point: 154-156°C
Density: 0.93 g/mL at 20 °C(lit.)
Refractive index: n20/D 1.496
Fp: 135°C
Storage temp.: Refrigerator
Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
Pka: 15.04±0.29(Predicted)
Form: Liquid
Color: Clear Colourless
Odor: at 100.00 %. mild floral peppery balsamic clean
Odor Type: floral
Water Solubility: Soluble in alcohol, natural, mineral and synthetic oils. Insoluble in water.
Merck: 14,1241
BRN: 5733954
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
LogP: 5.63
CAS DataBase Reference: 515-69-5(CAS DataBase Reference)
NIST Chemistry Reference: Bisabolol(515-69-5)
EPA Substance Registry System: Bisabolol (.alpha.R,1R)-rel- (515-69-5)
Uses
Bisabolol finds its application as a masking agent, skin conditioning agent and soothing agent in cosmetics industry.
The most important effects of Bisabolol for the use in cosmetics are anti-inflammatory, wound-healing, anti-bacterial and anti-mycotic.
Bisabolol is therefore perfectly suited for the use in all kinds of skin-care products.
Bisabolol can be used as active substance in cosmetic preparations for the protection and care of sensitive skin, preparations for babies and children, sunscreen and after-sun products, aftershaves and preparations for the oral hygiene.
Bisabolol is a botanical used for its anti-inflammatory and soothing properties.
Bisabolol is derived from chamomile and/or yarrow.
Bisabolol is an oil soluble ingredient, and can be used in a wide variety of oil based products including creams, serums, lotions, balms and hair products.
Bisabolol is a safe ingredient used in a wide array of formulations.
Bisabolol is safely used up to 1% concentration in leave-on formulations.
Skin care: Bisabolol has skin healing properties including reducing wrinkles and skin roughness, and repairing sun-damaged skin, and more recently it has been compounded with tretinoin as a topical treatment for acne.
Because of its anti-oxidant qualities, bisabolol can help keep skin firm and youthful-looking by visibly reducing the signs of aging.
Due to its anti-inflammatory qualities, it frequently plays a bioactive skin-calming role and is found in many products made for sensitive skin.
In addition to its calming effects, research suggests bisabolol may have some ability to lighten discoloration.
Bisabolol provides moisturization and relieves dry and itchy, flaky skin.
Hair care: Because of its high panthenol concentration, Bisabolol can effectively stimulate and promote the skin's healing process and encourage healthy hair growth.
Preparation
Via Nerolidol plus glacial Acetic acid with Sulfuric acid to yield Bisabolol acetate, Saponification of that ester yields Bisabolol.
rac-Bisabolol is produced by acid-catalyzed cyclization of farnesol or nerolidol.
The individual enantiomers are obtained by extraction from the appropriate plants.
