93861-30-4

Basic information

• Product Name: [1S,2R,4R,(+)]-p-Menthane-1,2,8-triol
• Synonyms: (1S,4R)-p-Menthane-1α,2α,8-triol;[1S,2R,4R,(+)]-4α-(1-Hydroxy-1-methylethyl)-1-methyl-1α,2α-cyclohexanediol;[1S,2R,4R,(+)]-p-Menthane-1,2,8-triol
• CAS NO: 93861-30-4
• Molecular Formula: C₁₀H₂₀O₃
• Molecular Weight: 0
• Mol File: 93861-30-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [1S,2R,4R,(+)]-p-Menthane-1,2,8-triol(CAS DataBase Reference)
• NIST Chemistry Reference: [1S,2R,4R,(+)]-p-Menthane-1,2,8-triol(93861-30-4)
• EPA Substance Registry System: [1S,2R,4R,(+)]-p-Menthane-1,2,8-triol(93861-30-4)

Safety Data

• Hazardous Substances Data: 93861-30-4(Hazardous Substances Data)

Upstream product

• 145105-47-1 4,4,8-trimethyl-2,3-dioxabicyclo<3.3.1>nonane-8-ol 
• 54145-81-2 1,2-epoxy-8-hydroxy-p-menthane 
• 80-26-2 terpinyl acetate 
• 7785-53-7 4R-α-terpineol 
• 91547-99-8 (1R,2S,4R)-1,2-epoxy-p-menthan-8-ol 
• 67225-28-9 (1R,2R,5R)-2,6,6-trimethyl-7-oxa-bicyclo<3.1.1>octan-2-ol 
• 93787-83-8 α-terpineol benzoate 
• 93787-84-9 acetoxypinol 

Downstream Products

• 5729-92-0 (1S,2R,4R)-4-isopropyl-1-methylcyclohexane-1,2-diol 
• 4436-81-1 homoterpenylmethylketone 
• 59121-74-3 (1S,2R,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol 

Relevant articles and documents

Selective Isomerization via Transient Thermodynamic Control: Dynamic Epimerization of trans to cis Diols

Traditional approaches to stereoselective synthesis require high levels of enantio- and diastereocontrol in every step that forms a new stereocenter. Here, we report an alternative approach, in which the stereochemistry of organic substrates is selectivel

Studies on the Oxidation of cis- and trans-Pinane with Molecular Oxygen

The pinanes are preferably attacked at the tertiary C-H bond in 2-position, but products of the oxidative attack at the secondary C-H-bonds in 3- and 4-position are also found.At 100 deg C cis-pinane is attacked more easily than trans-pinane (kcis : ktrans = 6.4), the relative rates of attack at the secondary C-H bonds in positions 3 and 4 with respect to the tertiary C-H bond in 2-position were also determined (in cis-pinane ksec : ktert = 0.027; in trans-pinane ksec : ktert = 0.20).After the attack at the 2-C-H bond the radical formed can either react with oxygen to form the corresponding cis- and trans-peroxy radicals and further to give cis- and trans-2-hydroperoxy pinane or fragmentate to the monocyclic radical derived from α-terpinene, giving as a final products α-terpinene hydroperoxide and the bicyclic 8-hydroperoxy 4,4,8-trimethyl 2,3-dioxabicyclononane.The corresponding alcohols were found after reduction with sodium sulphite.The oxidation at position 2 of the pinanes delivers not only the cis- and trans-hydroperoxide but also, as short-lived intermediates, the corresponding 2-pinanyloxy radicals.These radicals fragmentate forming a carbon radical with cyclobutane structure whose oxidation products were identified.Besides fragmentation of the 2-pinanyloxy radical also an intramolecular H-transfer from the methyl group in 9-position to the oxygen of the trans-pinanyloxy radical takes place leading to 9-hydroperoxy trans-pinane-2-ol.