72445-42-2

Usage

Uses

Used in Pharmaceutical Industry:
(1S,8aα)-Decahydro-3aα-methyl-7-methylene-1-isopropyl-4α,8α-epithioazulene is used as a pharmaceutical agent for its potent anticancer properties. It selectively and effectively inhibits the translation of oncogenic proteins, leading to the suppression of tumor growth and progression. Its unique mechanism of action and high potency make it a promising candidate for the development of new anticancer drugs.
Used in Traditional Medicine:
(1S,8aα)-Decahydro-3aα-methyl-7-methylene-1-isopropyl-4α,8α-epithioazulene is used in traditional medicine for its antitumor effects. It has been found in the bark of the Aglaia species of trees, particularly in parts of Southeast Asia, and has been utilized for its potential to suppress tumor growth and progression.

InChI:InChI=1/C15H24S/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(16-12)13(11)15/h9,11-14H,3,5-8H2,1-2,4H3/t11-,12-,13+,14-,15-/m0/s1

Upstream product

• 105453-16-5 germacrene D 
• 2158-59-0 cryptone 
• 23986-74-5 germacrene D 
• 317819-80-0 (1Z,6Z,8S)-1-methyl-5-methylidene-8-propan-2-ylcyclodeca-1,6-diene 
• 90460-44-9 (E)-4-Isopropyl-7-methylene-cyclodec-5-enone 
• 105359-04-4 Trifluoro-methanesulfonic acid (1Z,6E)-8-isopropyl-5-methylene-cyclodeca-1,6-dienyl ester 
• 90460-41-6 5-Isopropyl-8-methylene-2-vinyl-bicyclo[4.2.0]octan-2-ol 
• 90460-42-7 8-Isopropyl-bicyclo[7.1.1]undec-1⁽¹¹⁾-en-5-one 
• 90460-40-5 5-Isopropyl-8-methylene-bicyclo[4.2.0]octan-2-one 

Relevant academic research and scientific papers

The role of germacrene D as a precursor in sesquiterpene biosynthesis: Investigations of acid catalyzed, photochemically and thermally induced rearrangements

Germacrene D is considered as a precursor of many sesquiterpene hydrocarbons. We have investigated the acid catalyzed as well as the photochemically and thermally induced rearrangement processes of germacrene D isolated from several Solidago species, which contain both enantiomers of germacrene D. Enantiomeric mixtures of sesquiterpenes of the cadinane, eudesmane (selinane), oppositane, axane, isodaucane, and bourbonane group as well as isogermacrene D were identified as main products and made available as reference compounds for structure investigations and stereochemical assignments of plant constituents. δ-Amorphene, one of the rearrangement products, was identified as a natural product for the first time. The absolute configuration of γ-amorphene was revised by correlation with the absolute configuration of germacrene D. The mechanisms of the rearrangement reactions are discussed. (C) 2000 Elsevier Science Ltd.

CONFORMATIONAL CONTROL OF ENOLATE GEOMETRY: A SHORT SYNTHESIS OF GERMACRENE-D

A synthesis of (+/-)-germacrene-D is reported that employs a site- and stereoselective enolization of a conformationally biased ten-membered ring ketone.

Synthesis and Distribution of (-)-Mintsulfide, a Novel Sulfur-containing Sesquiterpene

(-)-Mintsulfide , a new sulfur-containing sesquiterpene found in peppermint oil, was synthesized from (-)-germacrene-D by a photochemical reaction and was confirmed to be (1R)-cis-2,6-epithio-cis-8-isopropyl-1-methyl-5-methylene-cis-bicyclo--decane.The existence of 1 was confirmed in 13 of 74 essential oils analyzed.

Sulphide Extrusion from Methyl Sulphonium Salts of the Sulphur-bridged Sesquiterpenes, Mintsulphide and Isomintsulphide by Alkyl-lithium

Reaction of the methylsulphonium salts of mintsulphide (1) and isomintsulphide (2) with methyllithium gives the desulphurization products, via the biradical intermediates, and the sigmatropic rearrangement products.