Pimelic acid

Base Information

• Chemical Name: Pimelic acid
• CAS No.: 111-16-0
• Molecular Formula: C7H12O4
• Molecular Weight: 160.17
• Hs Code.: 29171990
• European Community (EC) Number: 203-840-8
• NSC Number: 30112
• UNII: BZQ96WX25F
• DSSTox Substance ID: DTXSID5021598
• Nikkaji Number: J5.105E
• Wikipedia: Pimelic_acid
• Wikidata: Q414420
• Metabolomics Workbench ID: 1973
• ChEMBL ID: CHEMBL1235351
• Mol file: 111-16-0.mol

Synonyms:Acid, Pimelic;Acids, Pimelic;Pimelic Acid;Pimelic Acids

Chemical Property of Pimelic acid

Chemical Property:

• Appearance/Colour: white crystal or crystal powder
• Vapor Pressure: 5.92E-06mmHg at 25°C
• Melting Point: 103-105 °C(lit.)
• Refractive Index: 1.4352 (estimate)
• Boiling Point: 212 °C10 mm Hg(lit.)
• PKA: 4.71(at 25℃)
• Flash Point: 181.9 °C
• PSA: 74.60000
• Density: 1.201 g/cm³
• LogP: 1.10610
• Storage Temp.: Store below +30°C.
• Solubility.: ethanol: 0.1 g/mL, clear to very faintly hazy
• Water Solubility.: 25 g/L (13 ºC)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 160.07355886
• Heavy Atom Count: 11
• Complexity: 125

Purity/Quality:

99% ^*data from raw suppliers

Pimelic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C(CCC(=O)O)CCC(=O)O
• Description: Pimelic acid is the organic compound with the formula HO2C(CH2)5CO2H which has been synthesized from cyclohexanone and from salicylic acid. In the former route, the additional carbon is supplied by dimethyloxalate, which reacts with the enolate.This acid (heptanedioic acid), from the Greek pimelh (pimele fat), as adipic acid, was isolated from oxidized fats. It was obtained in 1884 by Ganttner F et al. as a product of ricinoleic acid (hydroxylated oleic acid) from castor oil.
• Uses: The major uses of pimelic acid are in plasticizers and polymers. Pimelic Acid is a metabolite found in four biofluids from dairy cows that may be used as biomarkers of milk.

Technology Process of Pimelic acid

There total 192 articles about Pimelic 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: 80.0%

cycloheptanol (502-41-0) → heptanedioic acid (111-16-0) + cycloheptanone (502-42-1)

Guidance literature:

With oxygen; trifluoroacetic acid; sodium nitrite; at 0 - 20 ℃; for 12.25h; Product distribution / selectivity;

Reference yield: 65.0%

1-(2-methoxyvinyl)benzene (4747-15-3) + (E)-2-benzylidenecycloheptanone (88356-04-1) → heptanedioic acid (111-16-0) + benzaldehyde (100-52-7)

Guidance literature:

With ozone; In diethyl ether; at -70 ℃;

DOI:10.1021/jo00032a010

Reference yield: 60.0%

1-(2-methoxyvinyl)benzene (4747-15-3) + 2-[1-(2-Trifluoromethyl-phenyl)-meth-(E)-ylidene]-cycloheptanone (138955-59-6) → heptanedioic acid (111-16-0) + benzaldehyde (100-52-7)

Guidance literature:

With ozone; In diethyl ether; at -70 ℃;

DOI:10.1021/jo00032a010

upstream raw materials:

3-(tetrahydrofuran-2-yl)propanoic acid

oxacycloheptadec-8-en-2-one

1,5-dibromo-pentane

sodium cyanide

Downstream raw materials:

dimethyl 1,7-heptanedioate

heptanedioic acid di-p-tolyl ester

7-ethoxy-7-oxoheptanoic acid

diethyl pimelate

Refernces

• 1、 Yang, Bingyu,Leclercq, Lo?c,Schmitt, Véronique,Pera-Titus, Marc,Nardello-Rataj, Véronique. "Colloidal tectonics for tandem synergistic Pickering interfacial catalysis: Oxidative cleavage of cyclohexene oxide into adipic acid". . p. 501 - 507. Retrieved 2019.
• 2、 Prelog,V. et al.. "". . p. 1658 - 1671. Retrieved 1962.
• 3、 Sato, Kei. "Chemical compositions of secondary organic aerosol from the ozonolysis of cyclohexene in the absence of seed particles". . p. 1584 - 1585. Retrieved 2005.
• 4、 Meth-Cohn, Otto,Wang, Mei-Xiang. "Regioselective biotransformations of dinitriles using Rhodococcus sp. AJ270". . p. 3197 - 3204. Retrieved 1997.
• 5、 Aguirreche. "". . . Retrieved 1928.
• 6、 Hitora, Yuki,Takada, Kentaro,Okada, Shigeru,Ise, Yuji,Matsunaga, Shigeki. "(-)-Duryne and its homologues, cytotoxic acetylenes from a marine sponge Petrosia sp.". . p. 1262 - 1267. Retrieved 2011.
• 7、 English,Clapp. "". . p. 461. Retrieved 1947.
• 8、 -. "METHOD FOR PRODUCING DICARBOXYLIC ACID". Paragraph 0115. . Retrieved 2021/05/21.
• 9、 Beller, Matthias,Ge, Yao,Huang, Weiheng,Jackstell, Ralf,Liu, Jiawang,Neumann, Helfried,Yang, Ji. "Direct and Selective Synthesis of Adipic and Other Dicarboxylic Acids by Palladium-Catalyzed Carbonylation of Allylic Alcohols". supporting information. p. 20394 - 20398. Retrieved 2020/09/21.