trans-13-Octadecenoic acid

Base Information

• Chemical Name: trans-13-Octadecenoic acid
• CAS No.: 693-71-0
• Molecular Formula: C₁₈H₃₄O₂
• Molecular Weight: 282.467
• Hs Code.: 2916190090
• European Community (EC) Number: 631-337-7,636-216-2
• DSSTox Substance ID: DTXSID60880901
• Nikkaji Number: J637.885D,J327.306G
• Wikidata: Q82862277
• Metabolomics Workbench ID: 1219
• Mol file: 693-71-0.mol

Synonyms:13-octadecenoic acid;13-octadecenoic acid, (E)-isomer;13-octadecenoic acid, sodium salt, (Z)-isomer

Chemical Property of trans-13-Octadecenoic acid

Chemical Property:

• Boiling Point: 398.2±11.0 °C(Predicted)
• PKA: 4.78±0.10(Predicted)
• PSA: 37.30000
• Density: 0.899±0.06 g/cm3(Predicted)
• LogP: 6.10850
• Storage Temp.: −20°C
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 282.255880323
• Heavy Atom Count: 20
• Complexity: 234

Purity/Quality:

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

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC=CCCCCCCCCCCCC(=O)O
• Isomeric SMILES: CCCC/C=C/CCCCCCCCCCCC(=O)O

Technology Process of trans-13-Octadecenoic acid

There total 19 articles about trans-13-Octadecenoic 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: 93.0%

C16H29BrO2 (1448529-20-1) + ethylmagnesium chloride (2386-64-3) → trans-13-octadecenoic acid (693-71-0)

Guidance literature:

C₁₆H₂₉BrO₂; With tert-butylmagnesium chloride; In tetrahydrofuran; at -78 ℃; for 0.166667h; Inert atmosphere;

ethylmagnesium chloride; With 1-methyl-pyrrolidin-2-one; buta-1,3-diene; nickel dichloride; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1002/chem.201204222

Reference yield: 56.0%

pentanal (110-62-3) + (12-carboxydodecyl)triphenylphosphonium bromide → (13Z)-octadec-13-enoic acid (693-71-0,7378-89-4,13126-39-1)

Guidance literature:

(12-carboxydodecyl)triphenylphosphonium bromide; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 - 20 ℃; for 2h; Inert atmosphere;

pentanal; In tetrahydrofuran; toluene; at -78 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.carres.2019.107748

Reference yield:

ethyl (13Z)-octadec-13-enoate → (13Z)-octadec-13-enoic acid (693-71-0,7378-89-4,13126-39-1)

Guidance literature:

With water; sodium hydroxide; at 20 ℃; for 3h;

DOI:10.1021/acschemneuro.7b00105

upstream raw materials:

13-oxotridecanoic acid

pentyltriphenylphosphonium bromide

cis-13-docosenoic acid

13,14-dihydroxy-behenic acid

Downstream raw materials:

(Z)-13-octadecen-1-yl acetate

(Z)-octadec-13-en-1-ol

cis-13-octadecenoic acid, methyl ester

Refernces

• 1、 -. "NOVEL GLYCINE TRANSPORT INHIBITORS FOR THE TREATMENT OF PAIN". Page/Page column 54. . Retrieved 2018/08/12.
• 2、 Iwasaki, Takanori,Higashikawa, Kiyokazu,Reddy, Vutukuri P.,Ho, Willbe W. S.,Fujimoto, Yukari,Fukase, Koichi,Terao, Jun,Kuniyasu, Hitoshi,Kambe, Nobuaki. "Nickel-butadiene catalytic system for the cross-coupling of bromoalkanoic acids with alkyl grignard reagents: A practical and versatile method for preparing fatty acids". . p. 2956 - 2960. Retrieved 2013/03/28.