1616-86-0

Basic information

• Product Name: (1R,4aα)-Decahydro-2,5,5,8aβ-tetramethyl-1β-(3-methyl-2,4-pentadienyl)-naphthalen-2α-ol
• Synonyms: (1R,4aα)-Decahydro-2,5,5,8aβ-tetramethyl-1β-(3-methyl-2,4-pentadienyl)-naphthalen-2α-ol
• CAS NO: 1616-86-0
• Molecular Formula: C₂₀H₃₄O
• Molecular Weight: 290.48336
• Mol File: 1616-86-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 40-42 °C
• Boiling Point: 160 °C(Press: 0.5 Torr)
• Appearance: /
• Density: 0.9808 g/cm3
• PKA: 15.37±0.70(Predicted)
• CAS DataBase Reference: (1R,4aα)-Decahydro-2,5,5,8aβ-tetramethyl-1β-(3-methyl-2,4-pentadienyl)-naphthalen-2α-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4aα)-Decahydro-2,5,5,8aβ-tetramethyl-1β-(3-methyl-2,4-pentadienyl)-naphthalen-2α-ol(1616-86-0)
• EPA Substance Registry System: (1R,4aα)-Decahydro-2,5,5,8aβ-tetramethyl-1β-(3-methyl-2,4-pentadienyl)-naphthalen-2α-ol(1616-86-0)

Safety Data

• Hazardous Substances Data: 1616-86-0(Hazardous Substances Data)

Usage

General Description

(1R,4aα)-Decahydro-2,5,5,8aβ-tetramethyl-1β-(3-methyl-2,4-pentadienyl)-naphthalen-2α-ol is a complex chemical compound with a long name. It is a type of terpenoid, which is a class of natural products derived from isoprene units. This specific compound is a derivative of naphthalene and contains a complex arrangement of methyl and pentadienyl groups. The chemical structure suggests that it may have potential biological or pharmacological activity, as terpenoids are known to have a wide range of biological effects, including antiviral, antibacterial, and anti-inflammatory properties. Further research and analysis may be necessary to fully understand the potential uses and effects of this compound.

Upstream product

• 66778-13-0 lead styphnate monohydrate 
• 6699-20-3 (E,E,E)-geranylgeranyl diphosphate 
• 515-03-7 sclareol 
• 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 
• 22628-64-4 Acetic acid (1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-(3-methylene-pent-4-enyl)-decahydro-naphthalen-2-yl ester 

Downstream Products

• 10314-52-0 8a-hydroxy-13,14,15,16-tetranorlabdan-12-oic acid 
• 564-20-5 (3aR)-(+)-sclareolide 
• 59170-14-8 12α-Hydroxy-13-epi-manoyl oxide 
• 56682-25-8 (8R,12R,13R)-8,12-epoxy-13-hydroxylabd-14-ene 
• 56711-38-7 (8R,12S,13S)-8,12-epoxy-13-hydroxylabd-14-ene 
• 56711-39-8 (8R,12R,13R)-8,12-epoxy-13-hydroxylabd-14-ene 
• 56711-40-1 (12S,13S)-8,12-epoxy-14-labden-13-ol 
• 38419-75-9 (1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol 
• 564-20-5 (3aR)-(+)-sclareolide 
• 6790-58-5 (-)-ambroxide 
• 199438-59-0 8S-1,2-di-O-benzyl-3-(11'-hydroxydriman-11'-yl)-4-O-methylbenzenetriol 
• 199438-60-3 8S-1,2-di-O-benzyl-3-(9'-drimen-11'-yl)-4-O-methylbenzenetriol 
• 199438-57-8 8S-13,14,15,16-tetranorlabdan-12-al 
• 17990-20-4 (12Z)-Labda-8⁽¹⁷⁾,12,14-triene 

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.

Synthesis of ambergris fragrance chemicals from sclareol, involving palladium catalysed key steps

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