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ChemicalBook--->CAS DataBase List--->94-53-1

94-53-1

94-53-1 Structure

94-53-1 Structure
IdentificationMore
[Name]

Piperonylic acid
[CAS]

94-53-1
[Synonyms]

1,3-BENZODIOXOLE-5-CARBOXYLIC ACID
3,4-METHYLENDIOXYBENZOIC ACID
3,4-(METHYLENEDIOXY)BENZOIC ACID
AKOS 213-90
PIPERONYLIC ACID
PROTOCATECHUIC ACID METHYLENETHER
RARECHEM AL BO 0210
TIMTEC-BB SBB003897
3,4-dioxymethylenebenzoicacid
5-benzodioxolecarboxylicacid
Benzoic acid, 3,4-(methylenedioxy)-
Heliotropic acid
heliotropicacid
Protocatechuic acid methylene ether
3,4-(methylenedioxy)benzoic acid, piperonylic acid
Piperonylic acid, 98+%
PIPEROYLICACID
3,4-Methylendioxybenzoic acid 98%
β(3,4-methylenedioxy-styryl)acrylic acid
1,3-Benzodioxole-5-carboxylic acid 98%
[EINECS(EC#)]

202-342-8
[Molecular Formula]

C8H6O4
[MDL Number]

MFCD00005830
[Molecular Weight]

166.13
[MOL File]

94-53-1.mol
Chemical PropertiesBack Directory
[Appearance]

white to light yellow crystal powde
[Melting point ]

229-231 °C (lit.)
[Boiling point ]

254.32°C (rough estimate)
[density ]

1.3579 (rough estimate)
[refractive index ]

1.5090 (estimate)
[storage temp. ]

Sealed in dry,Room Temperature
[solubility ]

DMSO (Slightly), Methanol (Slightly)
[form ]

Powder
[pka]

4.35±0.20(Predicted)
[color ]

Off-white to beige
[Water Solubility ]

slightly soluble
[Detection Methods]

HPLC,NMR
[Merck ]

14,7477
[BRN ]

150206
[LogP]

0.810 (est)
[CAS DataBase Reference]

94-53-1(CAS DataBase Reference)
[NIST Chemistry Reference]

1,3-Benzodioxole-5-carboxylic acid(94-53-1)
[EPA Substance Registry System]

94-53-1(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xn,Xi
[Risk Statements ]

R22:Harmful if swallowed.
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes.
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S37/39:Wear suitable gloves and eye/face protection .
[WGK Germany ]

3
[RTECS ]

DF4912765
[Hazard Note ]

Irritant
[TSCA ]

Yes
[HS Code ]

29329970
[Hazardous Substances Data]

94-53-1(Hazardous Substances Data)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Potassium hydroxide-->Potassium permanganate-->Piperonyl aldehyde-->methyl 1,3-benzodioxole-5-carboxylate-->3,4-(methylenedioxy)benzenediazonium tetrafluoroborate-->Piperonylonitrile
[Preparation Products]

1,3-BENZODIOXOLE-5-CARBOTHIOAMIDE-->6-BROMO-3,4-METHYLENEDIOXYBENZOIC ACID-->2-[4-(1,3-Benzodioxol-5-ylmethyl)piperazin-1-yl]pyrimidine-->(1,3-BENZODIOXOL-5-YLCARBONYL)AMINO]ACETIC ACID-->5-(2H-1,3-benzodioxol-5-yl)-1,3,4-thiadiazol-2-amine
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Piperonylic acid(94-53-1).msds
Hazard InformationBack Directory
[Chemical Properties]

white to light yellow crystal powde
[Uses]

Piperonylic Acid is a compound closely mimicking the structure of transcinnamic acid involved in the phenylpropanoid pathway in plant physiology.
[Definition]

ChEBI: Piperonylic acid is a member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a carboxy group at position 5. It is a natural product isolated from several plant species. It is a selective mechanism-based inactivator of the trans-cinnamate 4-hydroxylase enzyme and exhibits antifungal and skin wound healing properties. It has a role as a plant metabolite, an EC 1.14.14.91 ( trans-cinnamate 4-monooxygenase) inhibitor, a vulnerary and an antifungal agent. It is a member of benzodioxoles, a monocarboxylic acid and an aromatic carboxylic acid. It is a conjugate acid of a piperonylate.
[Synthesis Reference(s)]

The Journal of Organic Chemistry, 40, p. 3803, 1975 DOI: 10.1021/jo00913a051
[Purification Methods]

Crystallise the acid from EtOH or water. [Beilstein 19/7 V 300.]
[References]

[1] OTTO RICHARD GOTTLIEB MAURO T M. Isolation of Piperonylic Acid from Ocotea pretiosa[J]. Nature, 1958, 182 4637: 742-743. DOI:10.1038/182742b0.
[2] SEUNG HYUN HAN. Piperonylic Acid Promotes Hair Growth by Activation of EGFR and Wnt/β-Catenin Pathway.[J]. International Journal of Molecular Sciences, 2024, 25 19. DOI:10.3390/ijms251910774.
[3] SCHALK. Piperonylic acid, a selective, mechanism-based inactivator of the trans-cinnamate 4-hydroxylase: A new tool to control the flux of metabolites in the phenylpropanoid pathway[J]. Plant Physiology, 1998, 118 1: 209-218. DOI:10.1104/pp.118.1.209.
Spectrum DetailBack Directory
[Spectrum Detail]

Piperonylic acid(94-53-1)MS
Piperonylic acid(94-53-1)1HNMR
Piperonylic acid(94-53-1)13CNMR
Piperonylic acid(94-53-1)IR1
Piperonylic acid(94-53-1)IR2
Piperonylic acid(94-53-1)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Piperonylic acid, 99%(94-53-1)
[Alfa Aesar]

Piperonylic acid, 98+%(94-53-1)
[Sigma Aldrich]

94-53-1(sigmaaldrich)
[TCI AMERICA]

Piperonylic Acid,>98.0%(GC)(T)(94-53-1)
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