66537-42-6

Basic information

• Product Name: [1S-(1alpha,3abeta,4alpha,8abeta,9S*)]-decahydro-4,8,8-trimethyl-1,4-methanoazulene-9-carboxaldehyde
• Synonyms: [1S-(1alpha,3abeta,4alpha,8abeta,9S*)]-decahydro-4,8,8-trimethyl-1,4-methanoazulene-9-carboxaldehyde;(1S,3aR,4S,8aS,9R)-Decahydro-4,8,8-trimethyl-1,4-methanoazulene-9-carbaldehyde;(1S,6S,7R,10S,11R)-1,5,5-Trimethyltricyclo[5.4.0.06,10]undecane-11-carbaldehyde;(1S,9R)-1α,2,3,3aα,4,5,6,7,8,8aα-Decahydro-4α,8,8-trimethyl-1,4-methanoazulene-9-carbaldehyde
• CAS NO: 66537-42-6
• Molecular Formula: C₁₅H₂₄O
• Molecular Weight: 220.35046
• EINECS: 266-395-9
• Mol File: 66537-42-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 286.7°Cat760mmHg
• Flash Point: 101.2°C
• Appearance: /
• Density: 1.015g/cm³
• CAS DataBase Reference: [1S-(1alpha,3abeta,4alpha,8abeta,9S*)]-decahydro-4,8,8-trimethyl-1,4-methanoazulene-9-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: [1S-(1alpha,3abeta,4alpha,8abeta,9S*)]-decahydro-4,8,8-trimethyl-1,4-methanoazulene-9-carboxaldehyde(66537-42-6)
• EPA Substance Registry System: [1S-(1alpha,3abeta,4alpha,8abeta,9S*)]-decahydro-4,8,8-trimethyl-1,4-methanoazulene-9-carboxaldehyde(66537-42-6)

Safety Data

• Hazardous Substances Data: 66537-42-6(Hazardous Substances Data)

Usage

Description

[1S-(1alpha,3abeta,4alpha,8abeta,9S)]-decahydro-4,8,8-trimethyl-1,4-methanoazulene-9-carboxaldehyde, also known as Longifolenaldehyde, is a complex organic compound with a unique molecular structure. It is an intermediate in the synthesis of Longifolene, a constituent of black cumin seed that has potential anticancer and antibacterial properties.

Uses

Used in Pharmaceutical Industry:
[1S-(1alpha,3abeta,4alpha,8abeta,9S)]-decahydro-4,8,8-trimethyl-1,4-methanoazulene-9-carboxaldehyde is used as an intermediate in the synthesis of Longifolene for its potential anticancer and antibacterial properties. Longifolene, being a constituent of black cumin seed, may exhibit therapeutic effects against various types of cancer and bacterial infections, making it a valuable compound for the development of new drugs and treatments in the pharmaceutical industry.

Upstream product

• 7732-18-5 water 
• 469-27-2 longifolan-15-ol 
• 71-43-2 benzene 
• 475-20-7 longifolene 

Downstream Products

• 15373-31-6 α-campholenonitrile 

Relevant articles and documents

Eudismic analysis of tricyclic sesquiterpenoid alcohols: Lead structures for the design of potent inhibitors of the human UDP-glucuronosyltransferase 2B7

The epimeric tricyclic sesquiterpenoid alcohols globulol, epiglobulol, cedrol, epicedrol, longifolol, and isolongifolol were investigated in their ability to inhibit the recombinant human UDP-glucuronosyltransferase (UGT) 2B7. The stereoisomers displayed rapidly reversible competitive inhibition, which was substrate-independent. Longifolol and its stereoisomer isolongifolol displayed the lowest competitive inhibition constants (Kic) of 23 and 26 nM, respectively. The Kic values of cedrol and its epimer epicedrol were 0.15 and 0.21 μM, those of globulol and epiglobulol were 5.4 and 4.0 μM, respectively. The diastereomeric alcohols exhibited nearly identical affinities toward UGT2B7 indicating that the spatial arrangement of the hydroxy group had no influence on the dissociation of the enzyme-terpenoid complex. The high affinities stemmed presumably from mere hydrophobic interactions between the hydrocarbon scaffold of the terpenoid alcohol and the binding site of the enzyme. Glucuronidation assays revealed that there were large differences in the rates at which the epimeric alcohols were conjugated. Therefore, the spatial arrangement of the hydroxy group controlled the rate of the UGT2B7-catalyzed reaction. The introduction of a methyl group into the side chain of isolongifolol and longifolol increased the steric hindrance. As a result, the rate of the UGT2B7-catalyzed reaction was decreased by more than 88%. The findings indicated that the rate of the UGT2B7-catalyzed glucuronidation is significantly controlled by stereochemical and steric factors. Considering the high inhibition levels exerted by the tricyclic sesquiterpenoid alcohols, these compounds might serve as valuable lead structures for the design of potent inhibitors for UGT2B7.

Camphor/Longicamphor and 7β-Formylnorlongifolane/7β-Acetylnorlongifolane Oximes: A Comparative Beckmann Rearrangement Study

Camphor oxime (3)/longicamphor oxime (4) have been shown to undergo Beckmann fragmentation on exposure to tosyl chloride in pyridine generating olefinic nitriles: 3->5+6 and 4->7+8+9; in the case of 4 this reaction provides an entry into the bicyclononane system characteristic of the secolongifolene diol fungal metabolite (10). 7β-Formylnorlongifolane oxime (14)/7β-acetylnorlongifolane oxime (15) when treated with the same Beckmann catalyst under similar conditions, afford the nitrile (16)/amide (17); on hydrolysis with base 17 gives the amine 18.Reaction of longicamphor (2) with hydroxylamine-O-sulfonic acid, however, a ffords the nitrogen-insertion product, α-longicamphidone (24) besides the fragmented nitrile (7).