8,9,15-Trihydroxypentadecane-1-carboxylic acid

Base Information

• Chemical Name: 8,9,15-Trihydroxypentadecane-1-carboxylic acid
• CAS No.: 533-87-9
• Molecular Formula: C16H32 O5
• Molecular Weight: 304.427
• Hs Code.: 29181998
• European Community (EC) Number: 208-578-8
• DSSTox Substance ID: DTXSID10878090
• Nikkaji Number: J415.371E
• Wikipedia: Aleuritic_acid
• Wikidata: Q4716536,Q106902866
• Mol file: 533-87-9.mol

Synonyms:9,10,16-trihydroxypalmitic acid;aleuritic acid;aleuritolic acid;aleuritolic acid, (R*,R*)-isomer;aleuritolic acid, (R*,S*)-(+-)-isomer

Chemical Property of 8,9,15-Trihydroxypentadecane-1-carboxylic acid

Chemical Property:

• Appearance/Colour: white to beige crystalline powder
• Vapor Pressure: 7.78E-13mmHg at 25°C
• Melting Point: 100-101 °C(lit.)
• Refractive Index: 1.498
• Boiling Point: 516.7 °C at 760 mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 280.4 °C
• PSA: 97.99000
• Density: 1.085 g/cm³
• LogP: 2.46630
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly, Heated), DMSO (Slightly), Ethyl Acetate (Slightly, Heated,
• Water Solubility.: Soluble in water, alcohol, acetic acid and acetone.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 15
• Exact Mass: 304.22497412
• Heavy Atom Count: 21
• Complexity: 245

Purity/Quality:

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

α-AleuriticAcid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Other Biomolecules
• Canonical SMILES: C(CCCC(C(CCCCCCO)O)O)CCCC(=O)O
• Isomeric SMILES: C(CCC[C@@H]([C@@H](CCCCCCO)O)O)CCCC(=O)O
• Uses: α-Aleuritic acid is a major ingredient of shellac and is also a starting reagent in the manufacture of perfumes.

Technology Process of 8,9,15-Trihydroxypentadecane-1-carboxylic acid

There total 15 articles about 8,9,15-Trihydroxypentadecane-1-carboxylic 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: 94.0%

methyl aleuritate → erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9)

Guidance literature:

With sodium hydroxide; In N,N-dimethyl-formamide; for 1h; Ambient temperature;

Reference yield:

16-hydroxy-9-hexadecenoic acid (1619-68-7,17278-80-7,18951-79-6) → threo-9,10,16-trihydroxyhexadecanoic acid (533-87-9,6949-98-0,17941-34-3,18299-27-9,18951-77-4,33098-98-5,33098-99-6,37179-76-3,37179-77-4)

Guidance literature:

With formic acid; dihydrogen peroxide;

Reference yield:

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → threo-9,10,16-trihydroxyhexadecanoic acid (533-87-9,6949-98-0,17941-34-3,18299-27-9,18951-77-4,33098-98-5,33098-99-6,37179-76-3,37179-77-4)

Guidance literature:

Multistep reaction; (i) aq. HCl, (ii) aq. NaOH;

upstream raw materials:

16-hydroxy-9-hexadecenoic acid

threo-9,10,16-trihydroxyhexadecanoic acid

peracetic acid

16-acetoxy-hexadec-9-enoic acid ethyl ester

Downstream raw materials:

threo-9.10-dihydroxy-palmitic acid

16-hydroxy-9-hexadecenoic acid

threo-9,10,16-trihydroxyhexadecanoic acid

DL-erythro-aleuritic acid

Refernces

• 1、 Sarkar,Shrivastava. "FT-IR Spectroscopic Studies on Aleuritic Acid". . p. 326 - 327. Retrieved 2007/10/03.
• 2、 Khurana, J. M.,Sehgal, Arti. "AN EFFICIENT AND CONVENIENT PROCEDURE FOR ESTER HYDROLYSIS". . p. 580 - 583. Retrieved 2007/10/02.