23089-26-1

Basic information

• Product Name: (-)-ALPHA-BISABOLOL
• Synonyms: theta)]-thet;A-(-)-BISABOLOL;CAMILLOL;BISABOLOL, A-(-)-;BISABOLOL OXIDE A;DRAGOSANTOL;HYDAGEN B;LEVOMENOL
• CAS NO: 23089-26-1
• Molecular Formula: C₁₅H₂₆O
• Molecular Weight: 222.37
• EINECS: 245-423-3
• Product Categories: Miscellaneous Natural Products
• Mol File: 23089-26-1.mol
• Article Data: 22

Chemical Properties

• Boiling Point: bp12 153°
• Flash Point: 135 °C
• Appearance: /
• Density: d20 0.9211
• Vapor Pressure: 4E-05mmHg at 25°C
• Refractive Index: n20/D 1.496
• Storage Temp.: ?20°C
• PKA: 15.04±0.29(Predicted)
• Water Solubility: 22mg/L at 20℃
• CAS DataBase Reference: (-)-ALPHA-BISABOLOL(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-ALPHA-BISABOLOL(23089-26-1)
• EPA Substance Registry System: (-)-ALPHA-BISABOLOL(23089-26-1)

Safety Data

• RIDADR: UN 3082 9 / PGIII
• WGK Germany: 3
• RTECS: MJ9685000
• Hazardous Substances Data: 23089-26-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 23089-26-1 differently. You can refer to the following data:
1. (-)-α-Bisabolol was used to investigate the leishmanicidal and cytotoxic activity of essential oil of Vanillosmopsis arborea.
2. Reference Standard in the analysis of herbal medicinal products

General Description

(-)-α-Bisabolol is the major constituent of essential oil from leaves of Hymenocrater yazdianus.

Flammability and Explosibility

Notclassified

Biochem/physiol Actions

α-Bisabolol is active against primary acute leukemia cells, including BCR-ABL(+) acute lymphoblastic leukemias. It is the inhibitor of voltage-dependent Ca(2+) channels in tracheal smooth muscle preparations of rat. It also inhibits human and rat glioma cell growth and survival. It is a potential new therapeutic agent against leishmaniasis.

InChI: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

Upstream product

• 62660-04-2 (4S,8R)-8,9-Epoxy-p-menth-1-ene 
• 213479-77-7 (S)-4-Isopropenyl-1-methylcyclohexene 7,8-epoxide 
• 16666-80-1 triphenylphosphonio-1-methylethanide 
• 18031-40-8 (S)-(-)-perillaldehyde 
• 19206-72-5 Phosphoric acid diphenyl ester (2Z,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyl ester 
• 80767-64-2 p-nitrobenzoate de trimethyl-3,7,11 dodecatriene-1,6 Z, 10-yl 
• 80767-65-3 p-nitrobenzoate de trimethyl-3,7,11 dodecatriene-1,6 E, 10-yl 
• 4602-84-0 farnesol 
• 80795-69-3 p-nitrobenzoate de trimethyl-3,7,11 dodecatriene-1,6 E, 10-yl (S) 
• 115-18-4 2-methyl-3-buten-2-ol 
• 537674-51-4 (S)-3-((S)-4-Methyl-cyclohex-3-enyl)-butane-1,3-diol 
• 38614-36-7 2-methylpropen-1-ylmagnesium bromide 
• 67-56-1 methanol 
• 79197-22-1 (2R,3R,4S,5R,6S)-2-methyl-6-{[(2S)-6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-yl]oxy}tetrahydro-2H-pyran-3,4,5-triol 

Downstream Products

• 116537-82-7 tetrahydro-α-bisabolol 
• 110715-85-0 (6R,1'S)-epi-hernandulcin 
• 110160-83-3 2,6-dichloro-2-(4-chloro-4-methyl-cyclohexyl)-6-methyl-heptane 
• 80767-66-4 p-nitrobenzoate de methyl-6 (1 (S) methyl-4 cyclohexene-3-yl)-2 (S) heptene-5 yl-2 (S) 
• 80767-67-5 alpha-bisabolyl formate 
• 80767-67-5 formiate de (-), α-bisabolol 
• 152321-70-5 norbisabolide 

Relevant articles and documents

Synthesis method of 3-methyl-2-butene-1-geranoil formate

The invention belongs to the technical field of chemical synthesis and particularly relates to a synthesis method of 3-methyl-2-butene-1-geranoil formate. According to the synthesis method of the 3-methyl-2-butene-1-geranoil formate and on the basis of the existing technical process, sodium hydrogen sulfite serves as a catalyst, the yield of a 3-methyl-2-butene-1-geranoil formate product is further increased, more preferably, reaction is conducted under the existence of ionic liquid, the reaction time is effectively increased besides the yield of the products is effectively increased, and higher product yield can be obtained within shorter time.

Enantioselective microbial synthesis of the indigenous natural product (-)-α-bisabolol by a sesquiterpene synthase from chamomile (Matricaria recutita)

(-)-α-Bisabolol, a sesquiterpene alcohol, is a major ingredient in the essential oil of chamomile (Matricaria recutita) and is used in many health products. The current supply of (-)-α-bisabolol is mainly dependent on the Brazilian candeia tree (Eremanthus erythropappus) by distillation or by chemical synthesis. However, the distillation method using the candeia tree is not sustainable, and chemical synthesis suffers from impurities arising from undesirable α-bisabolol isomers. Therefore enzymatic synthesis of (-)-α-bisabolol is a viable alternative. In the present study, a cDNA encoding (-)-α-bisabolol synthase (MrBBS) was identified from chamomile and used for enantioselective (-)-α-bisabolol synthesis in yeast. Chamomile MrBBS was identified by Illumina and 454 sequencing, followed by activity screening in yeast. When MrBBS was expressed in yeast, 8mg of α-bisabolol was synthesized de novo per litre of culture. The structure of purified α-bisabolol was elucidated as (S,S)- α-bisabolol [or (-)-α-bisabolol]. Although MrBBS possesses a putative chloroplast-targeting peptide, it was localized in the cytosol, and a deletion of its N-terminal 23 amino acids significantly reduced its stability and activity. Recombinant MrBBS showed kinetic properties comparable with those of other sesquiterpene synthases. These data provide compelling evidence that chamomile MrBBS synthesizes enantiopure (-)-α-bisabolol as a single sesquiterpene product, opening a biotechnological opportunity to produce (-)-α-bisabolol.

METHOD FOR PRODUCING BISABOLOL WHICH IS FARNESOL FREE OR IS LOW IN FARNESOL

The present invention relates to a method of producing pure or enriched bisabolol by separating substance mixtures comprising bisabolol and farnesol by selective esterification of farnesol and subsequent distillative separation. The invention relates specifically to a method as specified above comprising the selective transesterification of mixtures comprising formyl-bisabolol and formyl-farnesol and subsequent distillative separation. The present invention furthermore relates to a method of producing farnesol esters.