122620-72-8

Basic information

• Product Name: <5R-(trans)>-1-p-Menthene-5,8-diol
• Synonyms: <5R-(trans)>-1-p-Menthene-5,8-diol
• CAS NO: 122620-72-8
• Molecular Weight: 170.252
• Mol File: 122620-72-8.mol

Chemical Properties

• CAS DataBase Reference: <5R-(trans)>-1-p-Menthene-5,8-diol(CAS DataBase Reference)
• NIST Chemistry Reference: <5R-(trans)>-1-p-Menthene-5,8-diol(122620-72-8)
• EPA Substance Registry System: <5R-(trans)>-1-p-Menthene-5,8-diol(122620-72-8)

Safety Data

• Hazardous Substances Data: 122620-72-8(Hazardous Substances Data)

Upstream product

• 473-67-6 trans-verbenol 
• 122621-69-6 <1S-(1α,6β,10α)>-10-Bromo-3,3,5,5,9-pentamethyl-2,4-dioxabicyclo<4.4.0>dec-8-ene 
• 122554-34-1 <1R-(trans)>-3,3,5,5,9-Pentamethyl-2,4-dioxabicyclo<4.4.0>dec-8-ene 

Relevant articles and documents

Synthesis of Aristotelia-type alkaloids: Syntheses of the natural products (-)-serratenone and (+)-11,12-didehydromakonin-10-one

Two independent total syntheses of the Aristotelia alkaloid (-)-serratenone ((-)-1) are disclosed, one starting with (-)-α-pinene, the other one with (S)-α-terpineol. These correlations led to a revision of the originally proposed absolute configuration of the natural product. In the course of systematic investigations of the behavior of the indole alkaloids (+)-makomakine ((+)-18) and (-)-hobartine ((-)-22) towards oxidizing reagents, it was found that treatment with I2 leads to no less than five different products. Depending on the exact reaction conditions, each of them can be obtained as the major component in yields between 40 and 60%. One of these compounds was shown to be identical with the natural product (+)-11,12-didehydromakonin-10-one ((+)-28).

Selective Synthesis of trans- and cis-p-Mentha-1,8-dien-5-ol from trans-Verbenol

A selective synthesis of both trans- and cis-p-mentha-1,8-dien-5-ol from trans-verbenol is described.The sequence leading to trans-p-mentha-1,8-dien-5-ol consists of cleavage of the cyclobutane ring of pinene with N-bromosuccinimide in acetone to give the acetonide of 6-bromo-trans-p-menthene-5,8-diol, hydrodebromination with lithium aluminum hydride, and acidic treatment of the resultant acetonide of trans-p-menthene-5,8-diol. cis-p-Mentha-1,8-dien-5-ol is obtained by Swern oxidation of the trans-isomer and reduction of the resultant ketone with lithium tri-sec-butylborohydride.Acidic treatment of the acetonide of cis-p-menthene-5,8-diol (obtained from cis-verbenol) gives exclusively p-mentha-1(7),2-dien-8-ol.