Heliotropic acid

Names

[ CAS No. ]:
94-53-1

[ Name ]:
Heliotropic acid

[Synonym ]:
5-benzodioxolecarboxylicacid
3,4-(Methylenedioxy)benzoic acid
Piperonylic acid
RARECHEM AL BO 0210
Heliotropic acid
PIPEROYLICACID
heliotropicacid
3,4-methylenedioxybenzoic acid
T56 BO DO CHJ GVQ
Benzoic acid, 3,4-(methylenedioxy)-
3,4-methylene dioxybenzoic acid
3,4-methylenedioxybenzenecarboxylic acid
1,3-Benzodioxole-5-carboxylic acid
EINECS 202-342-8
MFCD00005830

Biological Activity

[Description]:

Piperonylic acid is a natural molecule bearing a methylenedioxy function that closely mimics the structure of trans-cinnamic acid. Piperonylic Acid is a selective, mechanism-based inactivator of the trans-cinnamate 4-Hydroxylase[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

[References]

[1]. Schalk M, et al, Werck-Reichhart D. 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. Plant Physiol. 1998;118(1):209‐218.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
324.6±31.0 °C at 760 mmHg

[ Melting Point ]:
229-231 °C(lit.)

[ Molecular Formula ]:
C₈H₆O₄

[ Molecular Weight ]:
166.131

[ Flash Point ]:
139.6±18.3 °C

[ Exact Mass ]:
166.026611

[ PSA ]:
55.76000

[ LogP ]:
1.31

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.612

[ Water Solubility ]:
slightly soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DF4912765

CHEMICAL NAME :: 1,3-Benzodioxole-5-carboxylic acid

CAS REGISTRY NUMBER :: 94-53-1

LAST UPDATED :: 199701

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C8-H6-O4

MOLECULAR WEIGHT :: 166.14

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 196,478,1976

Safety Information

[ Symbol ]:

GHS05, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H315-H318-H335

[ Precautionary Statements ]:
P261-P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22;R37/38;R41

[ Safety Phrases ]:
S26-S36/37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
DF4912765

[ HS Code ]:
29329970

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

[Study on the bioactive constituents of Piper wallichii].

Zhong Yao Cai 35(1) , 53-6, (2012)

To investigate the bioactive constituents in the stem of Piper wallichii.Compounds were separated by column chromatography of silica gel, ODS-A and Sephadex LH-20. Their structures were elucidated bas...

Pattern triggered immunity (PTI) in tobacco: isolation of activated genes suggests role of the phenylpropanoid pathway in inhibition of bacterial pathogens.

PLoS ONE 9(8) , e102869, (2014)

Pattern Triggered Immunity (PTI) or Basal Resistance (BR) is a potent, symptomless form of plant resistance. Upon inoculation of a plant with non-pathogens or pathogenicity-mutant bacteria, the induce...

Free and conjugated benzoic acid in tobacco plants and cell cultures. Induced accumulation upon elicitation of defense responses and role as salicylic acid precursors.

Plant Physiol. 125(1) , 318-28, (2001)

Salicylic acid (SA) is a key endogenous component of local and systemic disease resistance in plants. In this study, we investigated the role of benzoic acid (BA) as precursor of SA biosynthesis in to...