CAS 18457-55-1 Perilla alcohol (HCID 369312)

Substructure search Find similar structures

Basic information

CAS: 18457-55-1
Standard SMILES: C=C(C)[C@@H]1CC=C(CO)CC1
InChIKey: NDTYTMIUWGWIMO-SNVBAGLBSA-N
Molecular formula: C10H16O
Average molar mass: 152.23 g/mol
Monoisotopic mass: 152.12011513

Overview

(S)-(-)-perillyl alcohol is a perillyl alcohol in which the chiral centre has S configuration. It is an enantiomer of a (R)-(+)-perillyl alcohol.

Names & identifiers

Preferred name: Perilla alcohol
IUPAC: [(4S)-4-prop-1-en-2-ylcyclohexen-1-yl]methanol
English name: (-)-PERILLYL ALCOHOL
Molecular formula: C10H16O
Molecular weight: 152.23

Names & synonyms

(S)-(-)-Perillyl alcohol(S)-Perillyl alcoholPerilla alcoholPerycorolle(-)-Perilla alcohol1-Cyclohexene-1-methanol, 4-(1-methylethenyl)-, (4S)-(-)-p-Mentha-1,8-dien-7-ol3UL4QIY642CHEBI:10782RefChem:45669perilla alcohol, (S)-(-)-Perillyl alcohol

Show more names

FEMA 2664RARECHEM AL BD 0003()-Perillyl AlcoholL(-)-PERILLYL ALCOHOLPERILLYL ALCOHOL, (-)-

18457-55-1(S)-(4-(Prop-1-en-2-yl)cyclohex-1-en-1-yl)methanol(-)-Perillylalcohol(S)-(?)-Perillyl alcoholMFCD00062995[(4S)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol(S)-(-)-(4-Isopropenyl-1-cyclohexenyl)methanol[(4S)-4-prop-1-en-2-ylcyclohexen-1-yl]methanol

Database identifiers

CAS: 18457-55-1、536-59-4
PubChem CID: 369312
DTXSID: DTXSID001377983
ChEBI: CHEBI:10782
UNII: 3UL4QIY642

Properties

Computed structural properties

XLogP: 2.1
Topological polar surface area: 20.2 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 1
Rotatable bonds: 2
Heavy atoms: 11
Formal charge: 0
Complexity: 179

Experimental & physicochemical properties

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]

LogP3.17

Physicochemical properties

Boiling point: 119 · 119-121 °C11 mm Hg(lit.)
alpha: -101 o · -101o (NEAT)
Density: 0.96 g/mL · 0.96 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.501
Flash point: 230 °F · >230 °F
storage temp.: 2 · 2-8°C
solubility: Chloroform (Sparingly), Methanol (Sparingly)
pka: 14.85 · 14.85±0.10(Predicted)
form: Liquid
Specific Gravity: 0.96 · 0.960
color: Colourless
biological source: synthetic

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

F: 10
PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
rtecs: OS8395000
risk_code: 37/38-41-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-39-36
Storage Class: 10 - Combustible liquids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Pharmacology

Metabolism/MetabolitesPerillyl alcohol is a known human metabolite of (-)-limonene.

MeSH Pharmacological Classification · 2 items

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Uses & manufacturing

Use ClassificationFlavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Applications · 3 items

Description(–)-Perillyl alcohol is a monoterpene alcohol that has been found in lavender essential oil and has diverse biological activities. It reduces production of hydroperoxidienes and thiobarbituric acid reactive substances (TBARS) in vitro in a concentration-dependent manner. (–)-Perillyl alcohol inhibits PANC-1 pancreatic carcinoma cell and H-Ras-transformed fibroblast growth when used at a concentration of 1 mM. It also inhibits the growth of P. aeruginosa, E. coli, S. aureus, and C. albicans (MICs = 480-2,900 ppm).

Uses(-)-Perillyl Alcohol is a monoterpene that induces apoptosis in colon tumor cells. Also, it is used in preparation of terpene-vanilloid conjugates as anti-inflammatory agents.

General Description(S)-(-)-Perillyl alcohol is a monoterpenoid compound found in the essential oils of cherries, lavender and spearmint. It shows potent anticancer activity.