536-30-1

Basic information

• Product Name: (2S,4S)-p-Menth-6(1)-en-2-ol
• Synonyms: (2S,4S)-p-Menth-6(1)-en-2-ol;cis-Carvotanacetol
• CAS NO: 536-30-1
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25
• Mol File: 536-30-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,4S)-p-Menth-6(1)-en-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S)-p-Menth-6(1)-en-2-ol(536-30-1)
• EPA Substance Registry System: (2S,4S)-p-Menth-6(1)-en-2-ol(536-30-1)

Safety Data

• Hazardous Substances Data: 536-30-1(Hazardous Substances Data)

Usage

General Description

(2S,4S)-p-Menth-6(1)-en-2-ol, also known as (4S)-p-menth-1-en-6-ol, is a chemical compound belonging to the family of monoterpenoids. It is found in various essential oils, including those of basil and rosemary, and is responsible for their characteristic aroma. (2S,4S)-p-Menth-6(1)-en-2-ol has a molecular formula of C10H18O and a molecular weight of 154.25 g/mol. It has a chiral center at the 4th and 6th carbon, resulting in two stereoisomers, of which the (2S,4S) form is the one commonly found in nature. (2S,4S)-p-Menth-6(1)-en-2-ol has been used in the food and fragrance industries for its pleasant scent and flavor, and it also has potential pharmacological properties, including anti-inflammatory and antibacterial effects.

Upstream product

• 499-71-8 carvotanacetone 
• 7632-16-8 (2S,4S)-carveol 
• 555-31-7 aluminum isopropoxide 
• 67-63-0 isopropyl alcohol 
• 55449-12-2 2,2-Dimethyl-propionic acid (1S,5S)-5-isopropenyl-2-methyl-cyclohex-2-enyl ester 
• 22472-56-6 (-)-trans-(1R,5S)-5-isopropyl-2-methyl-2-cyclohexen-1-ol 
• 197657-73-1 trans-(1R,5S)-5-isopropyl-2-methyl-2-cyclohexen-1-yl 3,5-dinitrobenzoate 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 22564-72-3 Acetic acid (2R,3R,5R)-3-hydroxy-5-isopropyl-2-methyl-cyclohexyl ester 
• 22564-72-3 Acetic acid (2R,3S,5R)-3-hydroxy-5-isopropyl-2-methyl-cyclohexyl ester 
• 61585-35-1 p-menth-1-ene 
• 80-56-8 Pinene 
• 1600-27-7 mercury(II) diacetate 

Downstream Products

• 909271-67-6 cis-(1S,5S)-5-isopropyl-2-methyl-2-cyclohexen-1-yl 3,5-dinitrobenzoate 
• 43205-82-9 carvotanacetone 
• 31383-92-3 (4R,6S)-6-Bromo-4-isopropyl-1-methyl-cyclohexene 
• 31383-92-3 (4R,6R)-6-Bromo-4-isopropyl-1-methyl-cyclohexene 
• 55449-16-6 (4S,6S)-6-methoxy-p-menth-1-ene 
• 188660-64-2 (4S,6R)-4-Isopropyl-6-methoxy-1-methyl-cyclohexene 
• 188660-64-2 (4R,6R)-4-Isopropyl-6-methoxy-1-methyl-cyclohexene 
• 16741-95-0 p-menth-6-en-2-one semicarbazone 
• 1274795-53-7 2,2,2-trichloro-N-((1R,5R)-5-isopropyl-2-methylcyclohex-2-enyl)acetamide 
• 1274795-58-2 methyl (1R,5R)-5-isopropyl-2-methylcyclohex-2-enylcarbamate 
• 1274795-59-3 C₁₄H₂₅NO₃ 
• 1274795-60-6 C₁₈H₂₇NO₄ 

Relevant articles and documents

Asymmetric synthesis of the tricyclic core of calyciphylline A-type alkaloids via intramolecular [3 + 2] cycloaddition

Asymmetric synthesis of the [5-6-7] tricyclic system common to the Calyciphylline A-type alkaloids is reported, featuring Overman rearrangement, Heck cyclization, intramolecular [3 + 2] cycloaddition, diastereoselective hydrogenation, and Claisen rearrangement as strategic events. The approach is capable of installing the crucial carbonyl functionality as well as multiple stereogenic centers within a congested polycyclic ring skeleton.

Mitsunobu Reaction of Unbiased Cyclic Allylic Alcohols

The stereochemical inversion of unbiased allylic alcohols using triphenylphosphine, diethyl azodicarboxylate, and benzoic acid, commonly known as the Mitsunobu reaction, was studied in three different solvents with specific attention toward the product composition. The results generated for the Mitsunobu reaction of (R)-3-deuterio-2-cyclohexen-1-ol and the cis and trans isomers of 1-deuterio-5-methyl-2-cyclohexen-1-ol, 1-deuterio-5-tert-butyl-2-cyclohexen-1-ol, and optically active cis and trans 5-isopropyl-2-methyl-2-cyclohexen-1-ol all gave similar product distributions with respect to inversion and retention at the carbinol center as well-as syn and anti Sn2′ type addition when THF or benzene was used as the solvent (CH2Cl2 gave less selective product distributions). Interestingly, it was found that the quasi-equatorial and quasi-axial nature of the starting allylic alcohol does not appear to affect the product distribution for this reaction, nor does methyl substitution at the central carbon of the allylic alcohol. In all cases, significant amounts (8-28%) of non-SN2 type products were detected for these sterically unbiased allylic alcohols; only 72-77% of the product was from SN2 type reaction when sterically undemanding (R)-S-deuterio-2-cyclohexen-1-ol was subjected to Mitsunobu conditions.

LIGHT-MEDIATED TRANSFORMATIONS OF OLEFINS INTO ALCOHOLS: REACTIONS OF HYDROXYL RADICALS WITH CYCLOALKENES

Reactions of hydroxyl radicals, generated by photodecomposition of hydrogen peroxide in acetonitrile, with a wide variety of cycloalkenes have been examined.The results show that the major reaction is the addition of hydroxyl radicals to the less substituted end of the double bond, furnishing the secondary alcohols.The reactivity pattern and the observed regio- and stereoselectivity clearly reveal that the steric parameters associated with the substrates play a dominant role in directing the addition reactions.More importantly, this study led to the development of a new methodology for the facile conversions of olefins essentially into secondary alcohols, and includes a few examples which demonstrate the potential of the method.