Piperic acid

Base Information

• Chemical Name: Piperic acid
• CAS No.: 136-72-1
• Molecular Formula: C12H10 O4
• Molecular Weight: 218.209
• Hs Code.: 2932990090
• European Community (EC) Number: 226-118-4
• NSC Number: 129538
• UNII: GFG3FLA9UR
• DSSTox Substance ID: DTXSID801016979
• Nikkaji Number: J15.943C,J47.722B,J8.831E
• Wikipedia: Piperic_acid
• Wikidata: Q1111585
• Metabolomics Workbench ID: 55551
• ChEMBL ID: CHEMBL332122
• Mol file: 136-72-1.mol

Synonyms:piperic acid

Chemical Property of Piperic acid

Chemical Property:

• Melting Point: 216-2170C
• Refractive Index: 1.7160 (estimate)
• Boiling Point: 427.9°Cat760mmHg
• PKA: 4.37±0.10(Predicted)
• Flash Point: 171.4°C
• PSA: 55.76000
• Density: 1.34g/cm³
• LogP: 2.06930
• Storage Temp.: Refrigerator
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 218.05790880
• Heavy Atom Count: 16
• Complexity: 308

Purity/Quality:

98%Min ^*data from raw suppliers

(E,E)-PipericAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1OC2=C(O1)C=C(C=C2)C=CC=CC(=O)O
• Isomeric SMILES: C1OC2=C(O1)C=C(C=C2)/C=C/C=C/C(=O)O
• Uses: A metabolite of Piperine

Technology Process of Piperic acid

There total 33 articles about Piperic 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: 100.0%

all-trans-5-(3,4-Methylendioxyphenyl)-2,4-pentadiensaeureethylester (6091-43-6,56019-71-7,60578-08-7,60578-12-3,63657-07-8) → piperic acid (136-72-1)

Guidance literature:

With potassium hydroxide; In methanol; for 6h; Heating;

Reference yield: 98.0%

Piperine (94-62-2,7780-20-3) → piperic acid (136-72-1)

Guidance literature:

Piperine; With potassium hydroxide; for 48h; Reflux;

With acetic acid; In water;

DOI:10.1016/j.ejmech.2021.113800

Reference yield: 95.0%

2-oxa-3-oxobicyclo[2.2.0]hex-5-ene (22980-23-0) + (3,4-methylenedioxy)phenylmagnesium bromide (17680-04-5) → piperic acid (136-72-1)

Guidance literature:

(3,4-methylenedioxy)phenylmagnesium bromide; With copper(l) cyanide; lithium chloride; In tetrahydrofuran; at -78 - -40 ℃; Schlenk technique; Inert atmosphere;

2-oxa-3-oxobicyclo[2.2.0]hex-5-ene; In tetrahydrofuran; diethyl ether; at -30 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1055/s-0037-1611652

upstream raw materials:

piperonal

diethyl ethylidenemalonate

sodium acetate

acetic anhydride

Downstream raw materials:

3,4-Dihydroxybenzoic acid

Piperonylic acid

5-(3',4'-methylenedioxyphenyl)pentanoic acid

6-bromo-3,4-methylenedioxybenzaldehyde

Refernces

• 1、 Wani, Naiem Ahmad,Singh, Samsher,Farooq, Saleem,Shankar, Sudha,Koul, Surrinder,Khan, Inshad Ali,Rai, Rajkishor. "Amino acid amides of piperic acid (PA) and 4-ethylpiperic acid (EPA) as NorA efflux pump inhibitors of Staphylococcus aureus". . p. 4174 - 4178. Retrieved 2016.
• 2、 Philipova, Irena,Valcheva, Violeta,Mihaylova, Rositsa,Mateeva, Mina,Doytchinova, Irini,Stavrakov, Georgi. "Synthetic piperine amide analogs with antimycobacterial activity". . p. 763 - 768. Retrieved 2018.
• 3、 Costa, Sonia Soares,Mors, Walter B.. "AMIDES OF OTTONIA CORCOVADENSIS". . p. 1305 - 1308. Retrieved 1981.
• 4、 Sivashanmugam, Arthi,Velmathi, Sivan. "Synthesis, in vitro and in silico anti-bacterial analysis of piperine and piperic ester analogues". . p. 19 - 29. Retrieved 2021.
• 5、 Bauer, Adriano,Nam, Jun-Hyun,Maulide, Nuno. "A Short, Efficient, and Stereoselective Synthesis of Piperine and its Analogues". . p. 413 - 416. Retrieved 2019.
• 6、 Cui, Jian,Lee, David Yue-Wei,Liu, Jing,Liu, Tonghua,Wang, Yanli,Wu, Lili,Yao, Yuan. "Synthesis and biological activity of piperine derivatives as potential PPARγ agonists". . p. 2069 - 2078. Retrieved 2020.
• 7、 Amperayani, Karteek Rao,Kumar, Kottakki Naveen,Parimi, Uma Devi. "Synthesis and in vitro and in silico antimicrobial studies of novel piperine–pyridine analogs". . p. 3549 - 3564. Retrieved 2018.
• 8、 Athayde-Filho, Petr?nio,Barbosa-Filho, José Maria,Batista, Tatianne,Brito, Monalisa,Costa, Normando,Cruz, Ryldene,Ferreira, Rafael,Leite, Fagner,Lira, Bruno,Magalh?es, Hemerson,Mangueira, Vivianne,Moura, Ana Paula,Santos, Jephesson,Sobral, Marianna,Sousa, Tatyanna,Souza, Helivaldo,Veras, Robson,Vieira, Giciane. "Th1-biased immunomodulation and in vivo antitumor effect of a novel piperine analogue". . . Retrieved 2018.
• 9、 Tian, Xiangge,Zhou, Meirong,Ning, Jing,Deng, Xiaopeng,Feng, Lei,Huang, Huilian,Yao, Dahong,Ma, Xiaochi. "The development of novel cytochrome P450 2J2 (CYP2J2) inhibitor and the underlying interaction between inhibitor and CYP2J2". . p. 737 - 748. Retrieved 2021/03/16.
• 10、 -. "NOVEL COMPOUND FOR PREVENTING OR TREATING NEUROINFLAMMATORY DISEASE AND PHARMACEUTICAL COMPOSITION INCLUDING THE SAME". Paragraph 0090; 0091. . Retrieved 2021/06/01.