18457-55-1

Basic information

• Product Name: (-)-PERILLYL ALCOHOL
• Synonyms: (S)-(-)-Perillyl alcohol 96%;(-)-PERILLYL ALCOHOL;PERILLYL ALCOHOL, (-)-;(-)-P-MENTHA-1,8-DIENE-7-OL;(S)-4-ISOPROPENYL-1-CYCLOHEXENYLMETHANOL;(S)-P-MENTHA-1,8-DIEN-7-OL;(S)-(-)-PERILLYL ALCOHOL;(S)-PERILLYL ALCOHOL
• CAS NO: 18457-55-1
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• EINECS: 208-639-9
• Mol File: 18457-55-1.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 119-121 °C11 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.96 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.501
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Sparingly)
• PKA: 14.85±0.10(Predicted)
• BRN: 2501605
• CAS DataBase Reference: (-)-PERILLYL ALCOHOL(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-PERILLYL ALCOHOL(18457-55-1)
• EPA Substance Registry System: (-)-PERILLYL ALCOHOL(18457-55-1)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41-36/37/38
• Safety Statements: 26-39-36
• WGK Germany: 3
• RTECS: OS8395000
• F: 10
• Hazardous Substances Data: 18457-55-1(Hazardous Substances Data)

Usage

Description

(-)-Perillyl alcohol, also known as (S)-(-)-Perillyl alcohol, is a monoterpenoid compound found in the essential oils of cherries, lavender, and spearmint. It exhibits potent anticancer activity and possesses diverse biological properties.

Uses

Used in Cancer Therapy:
(-)-Perillyl alcohol is used as an anticancer agent for its ability to induce apoptosis in colon tumor cells. It demonstrates potent anticancer activity, making it a promising candidate for cancer treatment.
Used in Anti-Inflammatory Agents:
In the pharmaceutical industry, (-)-Perillyl alcohol is used in the preparation of terpene-vanilloid conjugates, which serve as anti-inflammatory agents. This application leverages its natural anti-inflammatory properties to develop effective treatments for various inflammatory conditions.
Used in Antioxidant Applications:
(-)-Perillyl alcohol is used as an antioxidant, as it reduces the production of hydroperoxides and thiobarbituric acid reactive substances (TBARS) in vitro in a concentration-dependent manner. This property makes it a valuable component in formulations designed to combat oxidative stress and related conditions.
Used in Antimicrobial Agents:
In the field of microbiology, (-)-Perillyl alcohol is used as an antimicrobial agent, as it inhibits the growth of various bacteria and fungi, including P. aeruginosa, E. coli, S. aureus, and C. albicans, with minimum inhibitory concentrations (MICs) ranging from 480 to 2,900 ppm. This makes it a potential candidate for use in antimicrobial treatments and products.

Upstream product

• 5989-54-8 (-)-(S)-limonene 
• 18031-40-8 (S)-(-)-perillaldehyde 
• 5989-27-5 D-limonene 
• 6485-40-1 (R)-Carvone 
• 852920-51-5 β-pinene α-oxide 
• 1333393-09-1 3,5-dinitrobenzoic acid 4-(S)-isopropenyl-cyclohex-1-enylmethyl ester 
• 56246-58-3 β-pinene oxide 
• 26460-67-3 (S)-methylperillate 
• 875-08-1 (-)-β-Pinenoxid 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 7785-70-8 (+)-α-pinene 
• 564-94-3 myrtenal 
• 19894-98-5 6,6-dimethyl-2-methylene-bicyclo[3.1.1]heptan-3-ol 
• 18172-67-3 beta-pinene 

Downstream Products

• 15111-96-3 (S)-(4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methyl acetate 
• 100692-55-5 dihydroperilla alcohol 
• 845620-16-8 Malonic acid (S)-4-isopropenyl-cyclohex-1-enylmethyl ester methyl ester 
• 1027081-47-5 ((S)-5-Isopropyl-2-methylene-cyclohexanesulfinyl)-benzene 
• 1026837-87-5 (5S)-5-isopropyl-2-methylene-1-(4-pentenyl)-1-phenylsulfonylcyclohexane 
• 675578-06-0 methyl (S)-6-[(tert-butyldiphenylsilyl)oxy]-4-isopropenylhexanoate 
• 675578-07-1 4-[2-(tert-butyldiphenylsilyloxy)ethyl]-5-methylene-6-heptenoic acid 
• 675578-27-5 methyl 4-[2-(tert-butyldiphenylsilyloxy)ethyl]-5-methylene-6-heptenoate 
• 141206-20-4 (S)-(-)-perillyl β-D-glucopyranoside 
• 23635-14-5 (s)-(-)-perillic acid 
• 146659-09-8 (S)-(-)-1-butoxymethyl-4-acetyl-1-cyclohexene 
• 146659-10-1 (S)-(-)-4-butoxymethyl-3-cyclohexene-1-carboxylic acid 
• 146658-96-0 (S)-(-)-1-pentyl-4-(2-propenyl)-1-cyclohexene 

Relevant articles and documents

Intramolecular [2 + 2] Cycloadditions of Alkyl(phenylthio)ketenes: Total Synthesis of (+)-Sphaerodiol

Asymmetric total synthesis of (+)-sphaerodiol (2) has been achieved. A key step is an intramolecular [2 + 2] cycloaddition of alkyl(phenylthio)ketene for rapid assembly of the decalin ring.

Catalytic Asymmetric Allylic Substitution with Copper(I) Homoenolates Generated from Cyclopropanols

By using copper(I) homoenolates as nucleophiles, which are generated through the ring-opening of 1-substituted cyclopropane-1-ols, a catalytic asymmetric allylic substitution with allyl phosphates is achieved in high to excellent yields with high enantioselectivity. Both 1-substituted cyclopropane-1-ols and allylic phosphates enjoy broad substrate scopes. Remarkably, various functional groups, such as ether, ester, tosylate, imide, alcohol, nitro, and carbamate are well tolerated. Moreover, the present method is nicely extended to the asymmetric construction of quaternary carbon centers. Some control experiments argue against a radical-based reaction mechanism and a catalytic cycle based on a two-electron process is proposed. Finally, the synthetic utilities of the product are showcased by means of the transformations of the terminal olefin group and the ketone group.

One-Pot Absolute Stereochemical Identification of Alcohols via Guanidinium Sulfate Crystallization

A novel technique for the absolute stereochemical determination of alcohols has been developed that uses crystallization of guanidinium salts of organosulfates. The simple one-pot, two-step process leverages facile formation of guandinium organosulfate single crystals for the straightforward determination of the absolute stereochemistry of enantiopure alcohols by means of X-ray crystallography. The strong hydrogen bonding network drives the stability of the crystal lattice and allows for a diverse range of organic alcohol substrates to be analyzed.

Perilla amine compound and its preparation and use (by machine translation)

The invention belongs to the field of medical technology, involves a series of formula I structure perilla amine compound and its preparation and use. The states the perilla amine compound includes pharmaceutically acceptable salts and solvates, and states the perilla amines containing the compound or its pharmaceutically acceptable salt as an active ingredient of the composition, can be used for treating cancer. The invention the perilla amine compounds and their pharmaceutically acceptable salts has better anti-cancer activity, its preparation method is simple and feasible, and easy to operate. (by machine translation)