25491-00-3

Basic information

• Product Name: [1S-(1alpha,3abeta,4alpha,8abeta,9R*)]-decahydro-4,8,8-trimethyl-1,4-methanoazulene-9-carboxaldehyde
• Synonyms: [1S-(1alpha,3abeta,4alpha,8abeta,9R*)]-decahydro-4,8,8-trimethyl-1,4-methanoazulene-9-carboxaldehyde;(1S,3aR,4S,8aS,9S)-Decahydro-4,8,8-trimethyl-1β,4β-methanoazulene-9-carbaldehyde;(1S,3aα,8aα,9S)-Decahydro-4,8,8-trimethyl-1β,4β-methanoazulene-9-carbaldehyde;(1S,6S,7R,10S,11S)-1,5,5-Trimethyltricyclo[5.4.0.06,10]undecane-11-carbaldehyde;Isolongifolal
• CAS NO: 25491-00-3
• Molecular Formula: C₁₅H₂₄O
• Molecular Weight: 220.35046
• EINECS: 247-027-6
• Mol File: 25491-00-3.mol
• Article Data: 4

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,9R*)]-decahydro-4,8,8-trimethyl-1,4-methanoazulene-9-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: [1S-(1alpha,3abeta,4alpha,8abeta,9R*)]-decahydro-4,8,8-trimethyl-1,4-methanoazulene-9-carboxaldehyde(25491-00-3)
• EPA Substance Registry System: [1S-(1alpha,3abeta,4alpha,8abeta,9R*)]-decahydro-4,8,8-trimethyl-1,4-methanoazulene-9-carboxaldehyde(25491-00-3)

Safety Data

• Hazardous Substances Data: 25491-00-3(Hazardous Substances Data)

Usage

General Description

"[1S-(1alpha,3abeta,4alpha,8abeta,9R*)]-decahydro-4,8,8-trimethyl-1,4-methanoazulene-9-carboxaldehyde" is a complex chemical compound with a long and specific name. It is a bicyclic sesquiterpene aldehyde that is derived from plants and is commonly found in essential oils. [1S-(1alpha,3abeta,4alpha,8abeta,9R*)]-decahydro-4,8,8-trimethyl-1,4-methanoazulene-9-carboxaldehyde has a unique molecular structure consisting of 10 carbon atoms and various functional groups, including a carboxaldehyde group. It is known for its pleasant, woody odor and is used in the fragrance and flavor industry. Additionally, it possesses potential biological activities and medicinal properties, making it a subject of interest in pharmaceutical research. Despite its lengthy and complicated name, this compound plays a significant role in various applications in the chemical, fragrance, and pharmaceutical industries.

Upstream product

• 13928-57-9 (7S)-longifolanoic acid-⁽¹⁵⁾-methyl ester 
• 475-20-7 longifolene 
• 1139-17-9 (-)-Isolongifolol 
• 7732-18-5 water 
• 469-27-2 longifolan-15-ol 
• 71-43-2 benzene 

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.

The ozonolysis of longifolene: A tool for the preparation of useful chiral compounds. Configuration determination of new stereogenic centers by NMR spectroscopy and X-ray crystallography

The ozonolysis of (+)-longifolene (1) in different solvents (Et2O, CH2Cl2, CHCl3, acetone) at -80° provided quantitatively longifolene epoxide (3) as a single diastereoisomer in which the O-atom is endopositioned (Scheme 2). Upon warming to room temperature, the epoxide remained stable only in acetone and was isolated as a low-melting crystalline compound. In CH2Cl2, Et2O, or CHCl3 solution, epoxide 3 rapidly rearranged to the isomeric enols 4 and 5, which underwent further rearrangement to give the exo-aldehyde 6. On standing for several weeks in CH2Cl2 solution, or in CHCl3 and Et2O as well, at room temperature, aldehyde 6 slowly rearranged into its epimer 7. The aldehydes 6 and 7 were isolated on the preparative scale for further synthetic use. The addition of methylmagnesium iodide to 6 and 7 provided the corresponding alcohols 13/14 and 15/16. respectively, which were isolated as pure diastereoisomers (Scheme 4). The configurations of the new chiral centers in 13-16 were determined by NMR methods and X-ray crystallography.