Labd-13-ene-8,15-diol

Base Information

• Chemical Name: Labd-13-ene-8,15-diol
• CAS No.: 10267-31-9
• Molecular Formula: C20H36O2
• Molecular Weight: 308.49864
• Mol file: 10267-31-9.mol

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

Chemical Property of Labd-13-ene-8,15-diol

Chemical Property:

• Boiling Point: 408.5±18.0 °C(Predicted)
• PKA: 14.45±0.10(Predicted)
• PSA: 40.46000
• Density: 0.959±0.06 g/cm3(Predicted)
• LogP: 4.69880

Purity/Quality:

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

(E)-Labd-13-ene-8,15-diol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (E)-Labd-13-ene-8,15-diol possesses antiviral and anticancer activities and has been the most effective growth inhibitor of murine leukemia cell lines P388.

Technology Process of Labd-13-ene-8,15-diol

There total 16 articles about Labd-13-ene-8,15-diol 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: 98.0%

isosclareyl diacetate (119987-19-8) → 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)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 25 ℃; for 2h;

DOI:10.1016/0040-4039(88)85323-1

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

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) + 8(17),13(E)-labdadien-15-ol (10395-43-4) + (E)-3-methyl-5-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)pent-2-en-1-ol (87563-33-5)

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:

methyl 8α-hydroxylabd-13E-ene-15-oate

isosclareyl diacetate

E-8α-hydroxylabd-13-ene-15-al

sclareol

Downstream raw materials:

sclareol oxide

8-hydroxy-15,16-dinor-labdan-13-one

(1R,2R,4aS,8aS)-1-(2-(benzyloxy)ethyl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol

(4aS,5S,8aS)-5-(2-Benzyloxy-ethyl)-1,1,4a-trimethyl-6-methylene-decahydro-naphthalene

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.
• 2、 Bol'shakova, V. I.,Shmidt, E. N.,Pentegova, V. A.. "BICYCLIC RESIN ACIDS OF THE OLEORESINS OF Pinus mugo AND P. strobus". . p. 260. Retrieved 2007/10/02.