2-Hydroxyoleic acid

Base Information

• Chemical Name: 2-Hydroxyoleic acid
• CAS No.: 56472-29-8
• Molecular Formula: C18H34O3
• Molecular Weight: 298.466
• European Community (EC) Number: 803-722-1
• UNII: OSV3KVO1BT
• DSSTox Substance ID: DTXSID00430863
• Nikkaji Number: J2.359.309B
• Wikidata: Q28816084
• NCI Thesaurus Code: C105401
• Metabolomics Workbench ID: 74954
• Mol file: 56472-29-8.mol

Synonyms:2-hydroxyoleic acid;2-OHOA compound

Chemical Property of 2-Hydroxyoleic acid

Chemical Property:

• Melting Point: 47-50oC
• PSA: 57.53000
• LogP: 5.07930
• Storage Temp.: room temp
• Solubility.: DMSO: >20mg/mL
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 298.25079494
• Heavy Atom Count: 21
• Complexity: 261

Purity/Quality:

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

2-Hydroxy Oleic Acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCCCC(C(=O)O)O
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCC(C(=O)O)O
• Recent EU Clinical Trials: A randomized, double-blind, placebo-controlled adjuvant trial in newly diagnosed primary glioblastoma subjects to assess the efficacy and safety of 2-hydroxyoleic acid (2-OHOA) in combination with radiotherapy and temozolomide standard of care treatment
• Uses: An oleic acid synthetic analog that is an effective non-toxic anticancer drug with a wide spectrum against different types of cancer. An antihypertensive. 2OHOA has been used as:a modulator of the sphingolipid and glycerophospholipid pathway to study its effects on myelination in mice Charcot–Marie–Tooth type 1A (CMT1A) myelinopathy and myelinating dorsal root ganglia culturesin biophysical studies to study its effects on artificial membranesto study its interactions with major membrane lipid films

Technology Process of 2-Hydroxyoleic acid

There total 2 articles about 2-Hydroxyoleic 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:

α-hydroxy-cis-Δ9-octadecenoic acid sodium salt → oleic acid,hydroxy (56472-29-8)

Guidance literature:

With hydrogenchloride; In tert-butyl methyl ether; water;

Reference yield:

cis-Octadecenoic acid (112-80-1,2027-47-6) → oleic acid,hydroxy (56472-29-8)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; oxygen; lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1002/(sici)1099-0690(199809)1998:9<2013::aid-ejoc2013>3.0.co;2-s

Reference yield:

oleic acid,hydroxy (56472-29-8) → (R)-nonane-1,3-diol (23433-07-0,121541-59-1,121541-65-9,121651-87-4)

Guidance literature:

Multistep reaction; (i) O₃, (ii) NaBH₄, aq. NaOH, MeOH;

DOI:10.1139/v60-266

upstream raw materials:

cis-Octadecenoic acid

Downstream raw materials:

(R)-nonane-1,3-diol

8(Z)-heptadecenoic acid

Refernces

• 1、 -. "METHOD FOR THE SYNTHESIS OF HYDROXY-TRIGLYCERIDES AND USES THEREOF FOR THE PREVENTION AND TREATMENT OF DISEASES". Page/Page column 23-24. . Retrieved 2016/06/06.