Piperonylic acid

Base Information

• Chemical Name: Piperonylic acid
• CAS No.: 94-53-1
• Deprecated CAS: 1160950-49-1
• Molecular Formula: C8H6O4
• Molecular Weight: 166.133
• Hs Code.: 29329970
• European Community (EC) Number: 202-342-8
• NSC Number: 10072
• UNII: QX3V1NO0KH
• DSSTox Substance ID: DTXSID6059104
• Nikkaji Number: J4.700G
• Wikidata: Q27185967
• Metabolomics Workbench ID: 45652
• ChEMBL ID: CHEMBL573781
• Mol file: 94-53-1.mol

Synonyms:3,4-(methylenedioxy)benzoic acid;piperonylic acid;piperonylic acid, sodium salt

Chemical Property of Piperonylic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 9.95E-05mmHg at 25°C
• Melting Point: 229-231 °C(lit.)
• Refractive Index: 1.612
• Boiling Point: 324.6 °C at 760 mmHg
• PKA: 4.35±0.20(Predicted)
• Flash Point: 139.6 °C
• PSA: 55.76000
• Density: 1.468 g/cm³
• LogP: 1.11350
• Storage Temp.: Store below +30°C.
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: slightly soluble
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 166.02660867
• Heavy Atom Count: 12
• Complexity: 192

Purity/Quality:

99%min ^*data from raw suppliers

Piperonylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-36/37/38
• Safety Statements: 26-36/37/39-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1OC2=C(O1)C=C(C=C2)C(=O)O
• Uses: Piperonylic Acid is a compound closely mimicking the structure of transcinnamic acid involved in the phenylpropanoid pathway in plant physiology.

Technology Process of Piperonylic acid

There total 156 articles about Piperonylic 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: 57.0%

isosafrole (120-58-1) → piperonal (120-57-0,30024-74-9) + Piperonylic acid (94-53-1) + 3,4-methylenedioxypropiophenone (28281-49-4)

Guidance literature:

With PhI(OAc)2/Al₂O₃; at 140 ℃; for 0.5h; Microwave irradiation;

DOI:10.1021/op060117t

Reference yield: 18.8%

piperonal (120-57-0,30024-74-9) → isovanillin (621-59-0) + piperonol (495-76-1) + Piperonylic acid (94-53-1) + 4-(Benzo[1,3]dioxol-5-ylmethoxy)-3-hydroxy-benzaldehyde (75437-95-5)

Guidance literature:

With sodium methylate; In dimethyl sulfoxide; at 150 ℃;

Reference yield: 17.6%

piperonal (120-57-0,30024-74-9) + sodium methylate (124-41-4) → isovanillin (621-59-0) + piperonol (495-76-1) + Piperonylic acid (94-53-1) + 4-(Benzo[1,3]dioxol-5-ylmethoxy)-3-hydroxy-benzaldehyde (75437-95-5)

Guidance literature:

In dimethyl sulfoxide; at 150 ℃;

upstream raw materials:

n-butyllithium

1,2-(methylenedioxy)-4-bromobenzene

diethyl ether

piperonal

Downstream raw materials:

N-(2,3,4-trimethoxyphenethyl)(3',4'-methylenedioxyphenyl)acetamide

ethyl 3-(benzo[d][1,3]dioxol-5-yl)-3-oxopropanoate

6,7-methylendioxy-3,4-diphenylisocoumarin

Benzo[1,3]dioxole-5-carboxylic acid 2-iodo-4,5-dimethoxy-benzyl ester

Refernces

• 1、 Filho et al.. "-". . p. 417,419. Retrieved 1973.
• 2、 Chen, Cheng,Cheng, Hua,Verpoort, Francis,Wang, Zhi-Qin,Wu, Zhe,Yuan, Ye,Zheng, Zhong-Hui. "Gram-scale synthesis of carboxylic acids via catalytic acceptorless dehydrogenative coupling of alcohols and hydroxides at an ultralow Ru loading". . . Retrieved 2021/12/13.
• 3、 Bhardwaj, Nivedita,Goel, Bharat,Indra, Arindam,Jain, Shreyans K.,Singh, Ajit Kumar,Tripathi, Nancy. "Ni-NiO heterojunctions: a versatile nanocatalyst for regioselective halogenation and oxidative esterification of aromatics". . p. 14177 - 14183. Retrieved 2021/08/16.