15-Hydroxydehydroabietic acid

Base Information

• Chemical Name: 15-Hydroxydehydroabietic acid
• CAS No.: 54113-95-0
• Molecular Formula: C20H28O3
• Molecular Weight: 316.441
• European Community (EC) Number: 803-849-2
• UNII: SJT5EC4FM4
• ChEMBL ID: CHEMBL598566
• DSSTox Substance ID: DTXSID201307837
• Metabolomics Workbench ID: 143287
• Nikkaji Number: J148.731K
• Pharos Ligand ID: 29FT7MH5T2F5
• Wikidata: Q76423847
• Mol file: 54113-95-0.mol

Synonyms:15-hydroxydehydroabietic acid;54113-95-0;15-HYDROXYDEHYDROABIETICACID;SJT5EC4FM4;15-Hydroxydehydroabietic-acid;CHEMBL598566;15-Hydroxydehydroabieta-18-oic acid;(1R,4aS,10aR)-7-(1-hydroxy-1-methyl-ethyl)-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid;(1R,4aS,10aR)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid;(1R,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-7-(1-hydroxy-1-methylethyl)-1,4a-dimethyl-1-phenanthrenecarboxylic acid;UNII-SJT5EC4FM4;15-hydrooxydehydroabietic acid;DTXSID201307837;HY-N1589;BDBM50465338;15-HYDROXY-DEHYDROABIETIC ACID;AKOS032948557;FS-9997;CS-0017237;D85163;15-Hydroxydehydroabietic acid, >=95% (LC/MS-ELSD);1-PHENANTHRENECARBOXYLIC ACID, 1,2,3,4,4A,9,10,10A-OCTAHYDRO-7-(1-HYDROXY-1-METHYLETHYL)-1,4A-DIMETHYL-, (1R-(1.ALPHA.,4A.BETA.,10A.ALPHA.))-;1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-7-(1-hydroxy-1-methylethyl)-1,4a-dimethyl-, (1R-(1alpha,4abeta,10aalpha))-;1-Phenanthrenecarboxylic acid,1,2,3,4,4a,9,10,10a-octahydro-7-(1-hydroxy-1-methylethyl)-1,4a-dimethyl-, [1R-(1,4a,10a)]-

Chemical Property of 15-Hydroxydehydroabietic acid

Chemical Property:

• PSA: 57.53000
• LogP: 4.00890
• Storage Temp.: ?20°C
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 316.20384475
• Heavy Atom Count: 23
• Complexity: 485

Purity/Quality:

Analysis control,HPLC≥98% ^*data from raw suppliers

15-Hydroxydehydroabietic acid ≥95% (LC/MS-ELSD) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-50
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCC(C1CCC3=C2C=CC(=C3)C(C)(C)O)(C)C(=O)O
• Isomeric SMILES: C[C@]12CCC[C@@]([C@@H]1CCC3=C2C=CC(=C3)C(C)(C)O)(C)C(=O)O

Technology Process of 15-Hydroxydehydroabietic acid

There total 1 articles about 15-Hydroxydehydroabietic 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:

dehydroabietic acid (1740-19-8) → 7β-hydroxyabieta-8,11,13-trien-18-oic acid (73609-55-9) + 7-oxy-8,11,13-abietatrien-18-oic acid (18684-55-4,155473-19-1) + 15-hydroxydehydroabietic acid (54113-95-0) + 15-hydroxy-7-oxo-8,11,13-abietatrien-18-oic acid (95416-25-4)

Guidance literature:

With Rhodococcus erythropolis IEGM 267; Microbiological reaction;

DOI:10.1070/MC2001v011n02ABEH001414

Reference yield:

benzyl bromide (100-39-0) + 15-hydroxydehydroabietic acid (54113-95-0) → benzyl 15-hydroxydehydroabietate

Guidance literature:

15-hydroxydehydroabietic acid; With potassium carbonate; In acetone; for 0.25h;

benzyl bromide; In acetone; at 60 ℃; for 3h;

DOI:10.1080/14756366.2019.1690481

Reference yield:

15-hydroxydehydroabietic acid (54113-95-0) → C29H34O7

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / acetone / 0.25 h

1.2: 3 h / 60 °C

2.1: acetic acid; sulfuric acid; tert.-butylhydroperoxide / 1 h / 50 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 80 °C

4.1: palladium 10% on activated carbon; hydrogen / methanol / 12 h / 20 °C / 7500.75 Torr

With tert.-butylhydroperoxide; sulfuric acid; palladium 10% on activated carbon; hydrogen; potassium carbonate; acetic acid; In methanol; N,N-dimethyl-formamide; acetone;

DOI:10.1080/14756366.2019.1690481

upstream raw materials:

dehydroabietic acid

Downstream raw materials:

abieta-8,11,13-triene-15,18-diol

Refernces