33029-18-4

Basic information

• Product Name: [6aS,(+)]-6aα,7,10,10aβ-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol
• Synonyms: [6aS,(+)]-6aα,7,10,10aβ-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol;d-Δ8-Tetrahydrocannabinol
• CAS NO: 33029-18-4
• Molecular Formula: C21H30O2
• Molecular Weight: 314.4617
• Mol File: 33029-18-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [6aS,(+)]-6aα,7,10,10aβ-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: [6aS,(+)]-6aα,7,10,10aβ-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol(33029-18-4)
• EPA Substance Registry System: [6aS,(+)]-6aα,7,10,10aβ-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol(33029-18-4)

Safety Data

• Hazardous Substances Data: 33029-18-4(Hazardous Substances Data)

Usage

Description

[6aS,(+)]-6aα,7,10,10aβ-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol, commonly known as delta-3-carene, is a naturally occurring terpene derived from various plants and essential oils such as rosemary, basil, and bell pepper. It is characterized by its sweet, woody, and citrus-like aroma and is recognized for its potential therapeutic properties, including anti-inflammatory effects and potential benefits for bone health.

Uses

Used in Perfumery and Cosmetics Industry:
Delta-3-carene is used as a fragrance ingredient for its sweet, woody, and citrus-like aroma, contributing to the pleasant scents in perfumes, soaps, and cosmetics.
Used in Pharmaceutical Applications:
Delta-3-carene is being researched for its anti-inflammatory properties, making it a potential candidate for the treatment of arthritis and other inflammatory conditions. Its ability to reduce inflammation may offer relief and improve the quality of life for patients suffering from these conditions.
Used in Orthopedic and Bone Health Applications:
Due to its potential to promote bone health and stimulate bone repair, delta-3-carene is being explored for use in orthopedic applications and products aimed at improving bone health and recovery from bone-related injuries or conditions.

Upstream product

• 1228576-65-5 (6aS,10aS)-1-methoxy-6,6,9-trimethyl-3-pentyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene 
• 491-05-4 trans/cis-isopiperitenol 
• 500-66-3 Olivetol 
• 247227-98-1 (1S,2S)-2',6'-dimethoxy-5-methyl-4'-pentyl-2-(prop-1-en-2-yl)-1,2,3,4-tetrahydro-1,1'-biphenyl 
• 112639-16-4 2-iodo-1,3-dimethoxy-5-pentylbenzene 

Relevant articles and documents

Protecting group free enantiospecific total syntheses of structurally diverse natural products of the tetrahydrocannabinoid family

A simple, highly diastereoselective, Lewis acid catalyzed Friedel-Crafts coupling of a cyclic allylic alcohol with resorcinol derivatives has been developed. The method was applied for the enantiospecific total syntheses of structurally diverse natural products such as machaeriol-D, Δ8-THC, Δ9-THC, epi-perrottetinene and their analogues. Synthesis of both natural products and their enantiomers has been achieved with high atom economy, in a protecting group free manner and in less than 6 steps, the longest linear sequence, in a very good overall yield starting from R-(+) and S-(-)-limonene.

High-pressure diels-alder cycloadditions between benzylideneacetones and 1,3-Butadienes: Application to the synthesis of (R,R)-(-)- and (S,S)-(+)-Δ8-tetrahydrocannabinol

High-pressure Diels-Alder reactions of various alkoxy/alkyl-substituted benzylideneacetones with methyl-1,3-butadienes are reported. Activation by high pressure (8-11 kbar) in combination with the mild Lewis acid HfCl 42THF allows these reactions to efficiently and regioselectively produce a series of ortho-substituted cyclohexenyl-benzene cycloadducts, that are useful precursors for the expeditious construction of the privileged 6,6-dimethyltetrahydro-6H-benzo[c]chromene skeleton. Application to the synthesis of Δ8-trans-THC in both enantiomeric pure forms is based on the successful resolution of selected cycloadduct by the SAMP-hydrazone method.