10267-31-9

Basic information

• Product Name: Labd-13-ene-8,15-diol
• Synonyms: Labd-13-ene-8,15-diol;(1R,2R,4aS,8aS)-1-((E)-5-hydroxy-3-Methylpent-3-en-1-yl)-2,5,5,8a-tetraMethyldecahydronaphthalen-2-ol;Labd-13(E)-ene-8α,15-diol
• CAS NO: 10267-31-9
• Molecular Formula: C20H36O2
• Molecular Weight: 308.49864
• Mol File: 10267-31-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 408.5±18.0 °C(Predicted)
• Appearance: /
• Density: 0.959±0.06 g/cm3(Predicted)
• PKA: 14.45±0.10(Predicted)
• CAS DataBase Reference: Labd-13-ene-8,15-diol(CAS DataBase Reference)
• NIST Chemistry Reference: Labd-13-ene-8,15-diol(10267-31-9)
• EPA Substance Registry System: Labd-13-ene-8,15-diol(10267-31-9)

Safety Data

• Hazardous Substances Data: 10267-31-9(Hazardous Substances Data)

Usage

Description

Labd-13-ene-8,15-diol, also known as (E)-Labd-13-ene-8,15-diol, is a naturally occurring organic compound with significant biological activities. It is characterized by its unique chemical structure, which includes a labdane skeleton with specific double bonds and hydroxyl groups. This structure endows it with potent antiviral and anticancer properties, making it a valuable compound for pharmaceutical and medical research.

Uses

Used in Pharmaceutical Industry:
Labd-13-ene-8,15-diol is used as an antiviral agent for its ability to inhibit viral replication and reduce the severity of viral infections. Its antiviral activity is attributed to its interaction with specific viral targets, thereby disrupting the viral life cycle and protecting host cells from infection.
Used in Oncology:
Labd-13-ene-8,15-diol is used as an anticancer agent, particularly effective against various types of cancer. It has been identified as a potent growth inhibitor of murine leukemia cell lines P388, suggesting its potential use in the treatment of leukemia and possibly other cancer types. The compound's anticancer activity is believed to be due to its ability to interfere with cancer cell growth and proliferation, leading to the suppression of tumor development.
Used in Drug Development:
Labd-13-ene-8,15-diol serves as a promising lead compound in the development of new pharmaceuticals targeting viral and cancer-related diseases. Its unique chemical structure and biological activities make it an attractive candidate for further research and optimization to enhance its therapeutic potential and selectivity.

Upstream product

• 89576-50-1 E-8α-hydroxylabd-13-ene-15-al 
• 6699-20-3 (E,E,E)-geranylgeranyl diphosphate 
• 39850-84-5 Acetic acid 1-[2-((1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-decahydro-naphthalen-1-yl)-ethyl]-1-methyl-allyl ester 
• 54274-72-5 (R)-5-((1R,2R,4aS,8aS)-2-acetoxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl acetate 
• 515-03-7 sclareol 
• 119987-19-8 isosclareyl diacetate 
• 10267-29-5 methyl 8α-hydroxylabd-13E-ene-15-oate 

Downstream Products

• 5153-92-4 sclareol oxide 
• 16736-51-9 8-hydroxy-15,16-dinor-labdan-13-one 
• 150267-49-5 (1R,2R,4aS,8aS)-1-(2-(benzyloxy)ethyl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol 
• 150267-50-8 (4aS,5S,8aS)-5-(2-Benzyloxy-ethyl)-1,1,4a-trimethyl-6-methylene-decahydro-naphthalene 
• 178394-54-2 C₂₃H₃₄O₂ 
• 38419-77-1 (4aS,6aR,11aR,11bS)-4,4,6a,11b-Tetramethyl-dodecahydro-7,9-dioxa-cyclohepta[a]naphthalene 
• 6790-58-5 (-)-ambroxide 
• 19889-09-9 (E)-5-((1R,2R,4aR,8aS)-2-Hydroxy-2,5,5,8a-tetramethyl-decahydro-naphthalen-1-yl)-3-methyl-pent-2-enal 

Relevant articles and documents

Bifunctional cis-abienol synthase from Abies balsamea discovered by transcriptome sequencing and its implications for diterpenoid fragrance production

The labdanoid diterpene alcohol cis-abienol is a major component of the aromatic oleoresin of balsam fir (Abies balsamea) and serves as a valuable bioproduct material for the fragrance industry. Using high-throughput 454 transcriptome sequencing and metabolite profiling of balsam fir bark tissue, we identified candidate diterpene synthase sequences for full-length cDNA cloning and functional characterization. We discovered a bifunctional class I/II cis-abienol synthase (AbCAS), along with the paralogous levopimaradiene/ abietadiene synthase and isopimaradiene synthase, all of which are members of the gymnosperm- specific TPS-d subfamily. The AbCAS-catalyzed formation of cis-abienol proceeds via cyclization and hydroxylation at carbon C-8 of a postulated carbocation intermediate in the class II active site, followed by cleavage of the diphosphate group and termination of the reaction sequence without further cyclization in the class I active site. This reaction mechanism is distinct from that of synthases of the isopimaradiene- or levopimaradiene/ abietadiene synthase type, which employ deprotonation reactions in the class II active site and secondary cyclizations in the class I active site, leading to tricyclic diterpenes. Comparative homology modeling suggested the active site residues Asp-348, Leu-617, Phe-696, and Gly-723 as potentially important for the specificity of AbCAS. As a class I/II bifunctional enzyme, AbCAS is a promising target for metabolic engineering of cis-abienol production.

Oxidative degradation of the sclareol side chain: hemisyntheses of ambergris derivatives using in the key steps palladium complexes or ruthenium tetroxide generated in situ

We report the hemisyntheses of various ambergris-type derivatives: ambraoxide 4, Ambrox 8, 13-methylambraoxide 13, ambraketal 14, norambraketal 15, non-norambraketal 16 and dioxepane 53.Sclareol 12 is used as starting material because it is currently available from Salvia sclarea.The key steps involve an oxidative degradation of the sclareol 12 side chain, using either palladium complexes or ruthenium tetroxide generated in situ. - Keywords: sclareol; Ambrox; ambraoxide; 13-methylambraoxide; ambraketal; norambraketal; nor-norambraketal; farnesylic aldehyde; palladium complex; ruthenium tetroxide generated in situ; oxidative degradation

BICYCLIC RESIN ACIDS OF THE OLEORESINS OF Pinus mugo AND P. strobus

-