58404-89-0

Basic information

• Product Name: (1alpha,2alpha,5beta,8beta)-4,4,8-trimethyltricyclo[6.3.1.02,5]dodecan-1-ol
• Synonyms: (1alpha,2alpha,5beta,8beta)-4,4,8-trimethyltricyclo[6.3.1.02,5]dodecan-1-ol;Ai3-26373;Einecs 261-237-5;Tricyclo(6.3.1.0(2,5))dodecan-1-ol, 4,4,8-trimethyl-, stereoisomer
• CAS NO: 58404-89-0
• Molecular Formula: C₁₅H₂₆O
• Molecular Weight: 222.36634
• EINECS: 261-237-5
• Mol File: 58404-89-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 295°Cat760mmHg
• Flash Point: 123.6°C
• Appearance: /
• Density: 1.011g/cm³
• CAS DataBase Reference: (1alpha,2alpha,5beta,8beta)-4,4,8-trimethyltricyclo[6.3.1.02,5]dodecan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1alpha,2alpha,5beta,8beta)-4,4,8-trimethyltricyclo[6.3.1.02,5]dodecan-1-ol(58404-89-0)
• EPA Substance Registry System: (1alpha,2alpha,5beta,8beta)-4,4,8-trimethyltricyclo[6.3.1.02,5]dodecan-1-ol(58404-89-0)

Safety Data

• Hazardous Substances Data: 58404-89-0(Hazardous Substances Data)

Usage

General Description

The chemical (1alpha,2alpha,5beta,8beta)-4,4,8-trimethyltricyclo[6.3.1.02,5]dodecan-1-ol, also known as patchoulol, is a sesquiterpene alcohol commonly found in essential oils. It is a colorless to pale yellow liquid with a woody, earthy, and musky odor. Patchoulol is used in the fragrance industry as a base note in perfumes and as a fixative to prolong the scent of other ingredients. It also has potential use in the pharmaceutical industry due to its anti-inflammatory and antimicrobial properties. Additionally, patchoulol has shown promise as an insect repellent and is being researched for its potential use in agricultural applications.

Upstream product

• 97673-50-2 caryolane chloride 
• 87-44-5 β-caryophyllene 
• 86377-29-9 1-methoxycaryolane 
• 67-56-1 methanol 
• 87-44-5 β-caryophyllene 
• 372-97-4 farnesyl pyrophosphate 

Downstream Products

• 469-91-0 Clovan 
• 511-83-1 Clovensaeure 
• 57082-24-3 caryophyllene acetate 

Relevant articles and documents

Exploiting the Synthetic Potential of Sesquiterpene Cyclases for Generating Unnatural Terpenoids

The substrate flexibility of eight purified sesquiterpene cyclases was evaluated using six new heteroatom-modified farnesyl pyrophosphates, and the formation of six new heteroatom-modified macrocyclic and tricyclic sesquiterpenoids is described. GC-O analysis revealed that tricyclic tetrahydrofuran exhibits an ethereal, peppery, and camphor-like olfactoric scent.

Heteropoly acid catalysts in the valorization of the essential oils: Acetoxylation of β-caryophyllene

H3PW12O40 (PW), the strongest heteropoly acid in the Keggin series, is an active and environmentally friendly catalyst for the liquid-phase conversion of β-caryophyllene (1) to β-caryolanyl acetate (2) in homogeneous and heterogeneous systems. An efficient and clean method for the synthesis of 2, providing a mixture containing two stereoisomeric β-caryolanyl acetates 2a and 2b, 2a/2b = 80/20 mol/mol, with 100% GC yield, has been developed using PW as a homogeneous catalyst under mild reaction conditions. The reaction occurs at 25 °C with a catalyst turnover number of 2000. The catalyst can be recovered without neutralization and reused without loss of activity and selectivity.

STABLE CARBOCATIONS FROM TERPENOIDS. VIII. MOLECULAR REARRANGEMENTS OF CARYOPHYLLENE AND CLOVENE IN SUPERACIDS

The conformational composition of caryophyllene was analyzed by the computational methods of molecular mechanics and also the 13C NMR spectra.The conformationally controlled reactions of caryophyllene in superacids lead to mixtures of tricyclic compounds with new types of skeletons, which can be produced as the sum of the products from the "quenching" of the ions formed from clovene and 1-substituted caryolanes under the same conditions.