(+)-Copalol

Base Information

• Chemical Name: (+)-Copalol
• CAS No.: 10395-43-4
• Molecular Formula: C20H34 O
• Molecular Weight: 290.489
• Mol file: 10395-43-4.mol

Synonyms:2-Penten-1-ol,5-(decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl)-3-methyl-, [1S-[1a(E),4ab,8aa]]-; Labda-8(20),13-dien-15-ol, (E)- (8CI); (+)-Copalol;9,10-anti-Copalol; Anticopalol; Copalol

Chemical Property of (+)-Copalol

Chemical Property:

• Boiling Point: 378.2±11.0 °C(Predicted)
• PKA: 14.44±0.10(Predicted)
• PSA: 20.23000
• Density: 0.94±0.1 g/cm3(Predicted)
• LogP: 5.50400

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+)-Copalol

There total 4 articles about (+)-Copalol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 40.0%

(E,E,E)-geranylgeranyl diphosphate (6699-20-3,13100-78-2,64732-91-8) → (+)-manool (596-85-0,29461-42-5,41357-91-9,106631-38-3,1438-62-6) + manool (596-85-0) + 8(17),13(E)-labdadien-15-ol (10395-43-4)

Guidance literature:

With DL-dithiothreitol; recombinant (+)-copalyl diphosphate synthase-GST fusion protein; recombinant Rv₃₃₇₈c enzyme from Mycobacterium tuberculosis; magnesium chloride; at 30 ℃; for 15h; pH=7.5; diastereoselective reaction; aq. buffer; Enzymatic reaction;

DOI:10.1039/c0ob00884b

Reference yield:

isopentyl pyrophosphate (358-71-4) + geranyl diphosphate (763-10-0) → 8(17),13(E)-labdadien-15-ol (10395-43-4)

Guidance literature:

Multi-step reaction with 2 steps

1: magnesium chloride; D,L-dithiothreitol; recombinant P_. verruculosum copalyl diphosphate synthase / aq. buffer / 30 °C / pH 7.5 / Enzymatic reaction

2: sodium acetate; acid phosphatase from potato / propan-1-ol / 37 °C

With acid phosphatase from potato; recombinant P_. verruculosum copalyl diphosphate synthase; sodium acetate; magnesium chloride; D,L-dithiothreitol; In propan-1-ol;

DOI:10.1002/cbic.201700445

Reference yield:

(E,E,E)-geranylgeranyl diphosphate (6699-20-3,13100-78-2,64732-91-8) → 8,15-dihydroxy-13E-labdane (3649-91-0,10267-30-8,10267-31-9,11056-03-4,13903-00-9,22338-63-2,22343-28-8,25532-83-6,26790-87-4,58917-32-1,79434-22-3,100349-53-9,100349-54-0) + labd-13E-en-8α,15-diol diphosphate (1000876-36-7) + 8(17),13(E)-labdadien-15-ol (10395-43-4)

Guidance literature:

With DL-dithiothreitol; abietadiene synthase mutant H₃₄₈A; potassium chloride; glycerol; magnesium chloride; In aq. phosphate buffer; pH=6.8; Enzymatic reaction;

DOI:10.1021/ol3026022

upstream raw materials:

(E,E,E)-geranylgeranyl diphosphate

isopentyl pyrophosphate

geranyl diphosphate

Downstream raw materials:

Toluene-4-sulfonic acid 3-((1R,2R,4aS,4bS,8aS,10aS)-2,4b,8,8,10a-pentamethyl-tetradecahydro-phenanthren-1-yl)-propyl ester

Refernces

• 1、 Criswell, Jared,Potter, Kevin,Shephard, Freya,Beale, Michael H.,Peters, Reuben J.. "A single residue change leads to a hydroxylated product from the class II diterpene cyclization catalyzed by abietadiene synthase". . p. 5828 - 5831. Retrieved 2013/02/23.