935670-67-0

Basic information

• Product Name: (1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol
• Synonyms: (1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol
• CAS NO: 935670-67-0
• Molecular Weight: 168.236
• Mol File: 935670-67-0.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: (1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol(935670-67-0)
• EPA Substance Registry System: (1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol(935670-67-0)

Safety Data

• Hazardous Substances Data: 935670-67-0(Hazardous Substances Data)

Upstream product

• 123-73-9 trans-Crotonaldehyde 
• 176705-36-5 (1R,2R,4S,5R,6S)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0^4.2]octan-5-ol 
• 90-02-8 salicylaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 459-57-4 4-fluorobenzaldehyde 
• 104-88-1 4-chlorobenzaldehyde 
• 555-16-8 4-nitrobenzaldehdye 
• 1122-91-4 4-bromo-benzaldehyde 
• 121-33-5 vanillin 
• 100-52-7 benzaldehyde 
• 66885-03-8 (+)-cis-verbenol epoxide 
• 90582-89-1 verbenole epoxide 
• 87791-01-3 (3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol) 
• 473-66-5 (1S)-(-)-verbenone 

Downstream Products

• 1292847-82-5 (2S,4aR,8R,8aR)-4a,5,8,8a-tetrahydro-2-(3-hydroxy-4-methoxyphenyl)-4,4,7-trimethyl-4H-1,3-benzodioxin-8-ol 
• 1292847-88-1 (2S,4R,4aR,8R,8aR)-2-(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8, 8a-hexahydro-2H-chromene-4,8-diol 
• 1292847-83-6 (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-2-(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-2H-chromene-4,8-diol 
• 1292847-76-7 (2R,4S,4aR,6S,7R,8aR,9S)-hexahydro-2,9-bis(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-2H-4,6-(epoxymethano)chromen-8(5H)-one 
• 1292847-84-7 (2S,4aR,8R,8aR)-4a,5,8,8a-tetrahydro-4,4,7-trimethyl-2-(3,4,5-trimethoxyphenyl)-4H-1,3-benzodioxin-8-ol 
• 1292847-87-0 (2S,4R,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-(3,4,5-trimethoxyphenyl)-2H-chromene-4,8-diol 
• 1292847-86-9 (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-(3,4,5-trimethoxyphenyl)-2H-chromene-4,8-diol 
• 1292847-85-8 (2R,4S,4aR,6S,7R,8aR,9S)-hexahydro-4,7-dimethyl-2,9-bis(3,4,5-trimethoxyphenyl)-2H-4,6-(epoxymethano)chromen-8(5H)-one 
• 1292847-81-4 (2S,4R,4aR,8R,8aR)-2-(4-hydroxy-3-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8, 8a-hexahydro-2H-chromene-4,8-diol 
• 1292847-80-3 (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-2-(4-hydroxy-3-methoxyphenyl)-4,7-dimethyl-2H-chromene-4,8-diol 
• 1298063-71-4 (1R,2S,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol 
• 1361452-98-3 (1R,5S,6R)-6-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enyl isonicotinate 
• 1307887-00-8 diacetate (1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol 
• 1415323-53-3 (2R,4S,4aR,6S,7R,8aR,9S)-4,7-dimethyl-2,9-bis(2,3,4-trimethoxyphenyl)hexahydro-2H-4,6-(epoxymethano)chromen-8(8aH)-one 

Relevant articles and documents

Unusual α-hydroxyaldehyde with a cyclopentane framework from verbenol epoxide

The isomerization of (-)-cis-verbenol epoxide in the presence of K10 clay forms optically active 2-(2,2-dimethylcyclopent- 3-enyl)-2-hydroxypropanal as one of the products.

Heterogeneous catalysis for transformation of biomass derived compounds beyond fuels: Synthesis of monoterpenoid dioxinols with analgesic activity

Catalytic synthesis of a dioxinol compound, (2S,4aR,8R,8aR)-4,4,7-trimethyl-2-phenyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ol, exhibiting analgesic activity was demonstrated over Fe-modified beta zeolite. During interactions between cis-verbenol oxide and benzaldehyde, two main reactions occurred. In the first reaction, namely isomerization of verbenol oxide both cyclopentenic hydroxyketone, oxetane as well as a cyclohexyl compound, (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol were formed. In the second parallel reaction the target compound was generated. The highest yield of the target compound was achieved in the reaction between verbenol oxide and benzaldehyde at their molar ratio of 1:133 with the bifunctional iron modified Fe-H-Beta-150 catalyst at 70 °C giving a much higher yield than reported earlier in the literature, being 46 mol-% at complete conversion of verbenol oxide.

Synthesis and analgesic activity of stereoisomers of 2-(3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols

2-(3(4)-Hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols were found recently to possess high analgesic activity and low acute toxicity. Stereoisomers of these compounds with high optical purity were synthesized from (+)- and (-)-α-pinenes for the first time in this work. The structure of (4S)-4b isomer was confirmed by the XRD data. Studies of analgesic activity of the resulting products demonstrated that neither the absolute configuration nor cis- or trans-arrangement of vicinal oxygen atoms plays a significant role in manifestation of analgesic effect by these isomers, while only (4S)-4b isomer, but not (4R)-4b demonstrated the analgesic effect.

Isomerization of bicyclic terpene epoxides into allylic alcohols without changing of the initial structure

A novel method of (1S,2R,3R,5R)-6,6-dimethyl-4-methylenebicyclo[3.1.1] heptane-2,3-diol synthesis, which is a valuable intermediate in the synthesis of a perspective potent anti-Parkinson drugs, in the presence of TiO2 was proposed. Catalytic activity of TiO2 in the bicyclic terpene epoxides isomerization to corresponding allylic alcohols without changing of the initial structure was demonstrated, contrary to titania-supported Au catalysts which promoted rearrangement with predominant formation of a cyclopentene α-hydroxy ketone.