labdanolic acid

Base Information

• Chemical Name: labdanolic acid
• CAS No.: 469-11-4
• Molecular Formula: C20H36O3
• Molecular Weight: 324.504
• Mol file: 469-11-4.mol

Synonyms:(13S)-8-Hydroxy-labdan-15-saeure;8-hydroxylabdan-15-oic acid;(-)-(3S)-5-((1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydro-1-naphthalenyl)-3-methylpentanoic acid;labdanoloic acid;(8R,13S)-8-Hydroxy-labdan-16-saeure;labdanolic acid;Labdanolsaeure;

Chemical Property of labdanolic acid

Chemical Property:

• PSA: 57.53000
• LogP: 4.87100

Purity/Quality:

Labdanolic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Labdanolic Acid is a natural compound from the Cistus ladaniferis plant and is used in the preparation of anti-inflammatory agents.

Technology Process of labdanolic acid

There total 11 articles about labdanolic acid 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: 75.0%

(+/-)-1β-<(3S)-4-cyano-3-methylbutyl>-2β,5,5,8aβ-tetramethyl-4aαH-decahydro-2α-naphthalenol (110259-70-6) → (+/-)-labdanolic acid (469-11-4,1891-81-2,1891-82-3,57538-23-5,86189-98-2,100194-81-8,110311-98-3,110311-99-4)

Guidance literature:

With dihydrogen peroxide; In sodium hydroxide; ethanol; water;

DOI:10.1248/cpb.34.3518

Reference yield: 60.3%

13(S)-labdan-8α,15-diol (10267-21-7) → (-)-(3S)-5-((1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydro-1-naphthalenyl)-3-methylpentanoic acid (469-11-4)

Guidance literature:

With Jones reagent; In acetone; at 0 ℃; for 2h;

DOI:10.1016/j.ejmech.2010.04.007

Reference yield:

(4aSR,8RS,8aRS)-8-hydroxy-1,4a,8a-trimethyl-4,4a,6,7,8,8a,9,10-octahydrophenanthren-2(3H)-one (72214-46-1) → (+/-)-labdanolic acid (469-11-4,1891-81-2,1891-82-3,57538-23-5,86189-98-2,100194-81-8,110311-98-3,110311-99-4)

Guidance literature:

Multi-step reaction with 10 steps

1: lithium metal/liquid ammonia / tetrahydrofuran; liquid ammonia / 2 h / Heating

2: 95 percent / 80percent hydrazine hydrate, potassium hydroxide / bis-(2-hydroxy-ethyl) ether / 1.) 170 deg C, 2 h; 2.) 230 deg C, 1 h

3: 98 percent / hydrogen / platinum oxide / acetic acid / 60 h / Ambient temperature

4: Jones reagent / acetone / 0.5 h / 0 °C

5: 61 percent / perbenzoic acid / CHCl₃ / 48 h / Ambient temperature

6: 72 percent / butyllithium/diisopropylamine / hexane; tetrahydrofuran / 2 h / Ambient temperature

7: lithium aluminium hydride / diethyl ether / 0.5 h / 0 °C

8: 87 percent / pyridine / 12 h / 0 °C

9: 93 percent / tributylamine / H₂O / 6 h / Heating

10: 75 percent / sodium hydroxide, 30percent hydrogen peroxide / H₂O; ethanol / 7.5 h / Heating

With pyridine; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; Perbenzoic acid; jones reagent; tributyl-amine; ammonia; hydrogen; dihydrogen peroxide; lithium; hydrazine hydrate; diisopropylamine; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; ethanol; hexane; chloroform; ammonia; water; acetic acid; acetone; diethylene glycol;

DOI:10.1246/bcsj.61.4023

upstream raw materials:

13(S)-labdan-8α,15-diol

(+/-)-1β-<(3S)-4-cyano-3-methylbutyl>-2β,5,5,8aβ-tetramethyl-4aαH-decahydro-2α-naphthalenol

(4aSR,8RS,8aRS)-8-hydroxy-1,4a,8a-trimethyl-4,4a,6,7,8,8a,9,10-octahydrophenanthren-2(3H)-one

(+/-)-4bβ,8,8,10aβ-tetramethyl-4aαH,8aαH-tetradecahydro-1β-phenanthrenol

Downstream raw materials:

methyl (5S,8R,9R,10S,13S)-8-hydroxylabdan-15-oate

sclareol oxide

(-)-ambroxide

(+/-)-labdane-8α,15-diol

Refernces

• 1、 Hirota, Hiroshi,Nakamura, Toshio,Tsuyuki, Takahiko,Takahashi, Takeyoshi. "Stereoselective Total Synthesis of (+/-)-Labdane-8α-15-diol and (+/-)-Eperuane-8β,15-diol". . p. 4023 - 4028. Retrieved 2007/10/02.