58917-32-1

Basic information

• Product Name: ent-labd-13E-ene-8,15-diol
• CAS NO: 58917-32-1
• Molecular Weight: 308.505
• Mol File: 58917-32-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: ent-labd-13E-ene-8,15-diol(CAS DataBase Reference)
• NIST Chemistry Reference: ent-labd-13E-ene-8,15-diol(58917-32-1)
• EPA Substance Registry System: ent-labd-13E-ene-8,15-diol(58917-32-1)

Safety Data

• Hazardous Substances Data: 58917-32-1(Hazardous Substances Data)

Upstream product

• 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 
• 89576-50-1 E-8α-hydroxylabd-13-ene-15-al 
• 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 
• 13008-80-5 (13S)-5β,9β,10α-Labd-8(20)-en-15-saeure-methylester; Eperusaeure-methylester 
• 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

A single residue change leads to a hydroxylated product from the class II diterpene cyclization catalyzed by abietadiene synthase

Class II diterpene cyclases catalyze bicyclization of geranylgeranyl diphosphate. While this reaction typically is terminated via methyl deprotonation to yield copalyl diphosphate, in rare cases hydroxylated bicycles are produced instead. Abietadiene synthase is a bifunctional diterpene cyclase that usually produces a copalyl diphosphate intermediate. Here it is shown that substitution of aspartate for a conserved histidine in the class II active site of abietadiene synthase leads to selective production of 8α-hydroxy-CPP instead, demonstrating striking plasticity.

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

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