12-Hydroxystearic acid

Base Information

• Chemical Name: 12-Hydroxystearic acid
• CAS No.: 18417-00-0
• Deprecated CAS: 36377-33-0,78642-86-1,8039-23-4,860114-96-1,1629856-01-4,654637-88-4,78642-86-1,860114-96-1
• Molecular Formula: C18H36 O3
• Molecular Weight: 300.482
• European Community (EC) Number: 203-366-1,253-004-1
• NSC Number: 2385
• UNII: 933ANU3H2S
• DSSTox Substance ID: DTXSID8026725
• Nikkaji Number: J48.641H
• Wikidata: Q10843743,Q27158401
• RXCUI: 1368628
• Metabolomics Workbench ID: 2166
• ChEMBL ID: CHEMBL292352
• Mol file: 18417-00-0.mol

Synonyms:12-hydroxy stearic acid

Chemical Property of 12-Hydroxystearic acid

Chemical Property:

• Boiling Point: 436.3°Cat760mmHg
• Flash Point: 231.8°C
• PSA: 57.53000
• Density: 0.944g/cm³
• LogP: 5.30330
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 16
• Exact Mass: 300.26644501
• Heavy Atom Count: 21
• Complexity: 229

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CCCCCCC(CCCCCCCCCCC(=O)O)O

Technology Process of 12-Hydroxystearic acid

There total 11 articles about 12-Hydroxystearic 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: 97.0%

Ricinoleic acid (141-22-0,27925-02-6,7431-95-0,84799-84-8) → R-12-hydroxyoctadecanoic acid (106-14-9,18417-00-0,36377-33-0,5762-36-7,78642-86-1,8039-23-4,27924-99-8,860114-96-1)

Guidance literature:

With hydrogen; Rh/Al₂O₃; In ethyl acetate; for 4.5h; Ambient temperature;

DOI:10.1016/S0009-3084(97)00085-6

Reference yield: 97.0%

C26H41NO6 → (12S)-12-hydroxyoctadecanoic acid (18417-00-0,78642-86-1,8039-23-4,27924-99-8,860114-96-1)

Guidance literature:

C₂₆H₄₁NO₆; With potassium hydroxide; In methanol; at 20 ℃; for 14h;

With hydrogenchloride; In water;

DOI:10.1021/jacs.8b00910

Reference yield: 81.0%

(S)-nonadec-18-en-7-ol (1033405-13-8) → (12S)-12-hydroxyoctadecanoic acid (18417-00-0,78642-86-1,8039-23-4,27924-99-8,860114-96-1)

Guidance literature:

(S)-nonadec-18-en-7-ol; With osmium(VIII) oxide; In N,N-dimethyl-formamide; tert-butyl alcohol; at 20 ℃; for 0.0833333h;

With oxone; In N,N-dimethyl-formamide; tert-butyl alcohol; at 20 ℃; optical yield given as %ee; chemoselective reaction;

DOI:10.1039/b801514g

upstream raw materials:

Ricinoleic acid

methyl (R)-12-hydroxyoctadecanoate

(R)-13-Hexyl-oxacyclotridecan-2-one

ethanol

Downstream raw materials:

(R)-12-acetoxy-octadecanoic acid-((Ξ)-2-ethyl-hexyl ester)

(R)-12-hydroxy-octadecanoic acid cholesteryl ester

(12S)-12-hydroxyoctadecanoic acid

5-hexyldihydro-2(3H)-furanone

Refernces

• 1、 Asai, Teigo,Fujimoto, Yoshinori. "Cyclic fatty acyl glycosides in the glandular trichome exudate of Silene gallica". experimental part. p. 1410 - 1417. Retrieved 2011/04/25.
• 2、 Weiper-Idelmann, Andreas,Aus Dem Kahmen, Martin,Schaefer, Hans J.,Gockeln, Marianne. "Electroorganic synthesis 65. Anodic homocoupling of carboxylic acids derived from fatty acids". . p. 672 - 682. Retrieved 2007/10/03.