.BETA.-CARYOPHYLLENE ALCOHOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H26O
Molecular Weight	222.3663
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of .BETA.-CARYOPHYLLENE ALCOHOL

Structure Search

SMILES

[H][C@]12CC(C)(C)[C@]1([H])CC[C@]3(C)CCC[C@@]2(O)C3

InChI

InChIKey=FUQAYSQLAOJBBC-PAPYEOQZSA-N

InChI=1S/C15H26O/c1-13(2)9-12-11(13)5-8-14(3)6-4-7-15(12,16)10-14/h11-12,16H,4-10H2,1-3H3/t11-,12+,14+,15-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C15H26O
Molecular Weight	222.3663
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18640216
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28891397 | https://www.ncbi.nlm.nih.gov/pubmed/28724695

beta-Caryophyllene alcohol is a fragrance ingredient used in decorative cosmetics, fine fragrances, shampoos, toilet soaps and other toiletries as well as in non-cosmetic products such as household cleaners and detergents. Its use worldwide is in the region of <0.1 metric tonnes per annum. In vivo studies found that b-Caryophyllene alcohol significantly inhibited asthma induced by histamine and acetylcholine in guinea pigs with the efficacy lasting for at least 6 hours and with the potency equivalent to aminophylline. Inhibition of airway inflammation and scavenging of free radical and reactive oxygen species was one of the mechanisms of anti-asthmatic action

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
reactive oxygen species biosynthetic process 37 Target ID: GO:1903409 Sources: http://en.cnki.com.cn/Article_en/CJFDTOTAL-YWSW200605013.htm	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28891397	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Fragrance material review on beta-caryophyllene alcohol.	2008 Nov	18640216

Patents

Sample Use Guides

In Vivo Use Guide

For intravenous (i.v.) pharmacokinetic studies, the rats were treated with low (5 mg/kg), middle (10 mg/kg) and high (20 mg/kg) doses of b-Caryophyllene alcohol solution (in 5% glucose containing 30% ethanol as solubilizer) via tail vein. For oral pharmacokinetic studies, the rats received an intragastric (i.g.) dose (100 mg/kg) of b-Caryophyllene alcohol solution, suspension (in 0.5% sodium carboxy-methylcellulose) and PEG formulation.

Route of Administration: Other

In Vitro Use Guide

S. griseus strain S4–7 was used for activity evaluation. To test antifungal activity, the volatile mixture concentration of S4–7 was prepared at 5 mg ml21 and 40, 20 and 10 ml samples used. The synthetic caryolan-1-ol was diluted to 0.075, 0.038, 0.019, 0.009 and 0.005 mmol ml21. A paper disc (8 mm) treated with a fraction of volatiles mixture or synthesized caryolan-1-ol was put in the lid of the Petri dish cover and B. cinerea was grown on the agar at 278C. After 4 days of incubation, mycelial growth was measured.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:39:50 GMT 2023` Edited by `admin` on `Sat Dec 16 01:39:50 GMT 2023`
Record UNII	9Y50O7OH2E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

.BETA.-CARYOPHYLLENE ALCOHOL

Common Name

English

CARYOPHYLLENE ALCOHOL [FHFI]

Common Name

English

CARYOLAN-1-OL

Common Name

English

.BETA.-CARYOLANOL

Common Name

English

CARYOLANOL-1

Systematic Name

English

TRICYCLO(6.3.1.02,5)DODECAN-1-OL, 4,4,8-TRIMETHYL-, (1R,2S,5R,8S)-

Systematic Name

English

FEMA NO. 4410

Code

English

Classification Tree Code System Code

JECFA EVALUATION

CARYOPHYLLENE ALCOHOL