4-methoxycinnamic acid

2-propenoic acid, 3-(4-methoxyphenyl)-

CAS: 830-09-1 C10 H10 O3 MW: 178.18730000

Identification

Name4-methoxycinnamic acid
IUPAC3-(4-methoxyphenyl)prop-2-enoic acid
CAS Number830-09-1
EINECS212-594-0
FDA UNII6G4ML8401A
Molecular FormulaC10 H10 O3
Molecular Weight178.18730000
MDL NumberMFCD00004398
XlogP32.10 (est)

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 342.59 °C. @ 760.00 mm Hg (est)
Flash Point 281.00 °F. TCC ( 138.60 °C. ) (est)
logP (o/w) 2.680
Soluble in water, 717.7 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintraperitoneal-mouse LD > 1300 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for 4-methoxycinnamic acid usage levels up tonot for fragrance use.
Recommendation for 4-methoxycinnamic acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

found in nature

Synonyms

cinnamic acid, 4-methoxy- cinnamic acid, p-methoxy- 4- methoxy cinnamic acid p- methoxycinnamic acid para- methoxycinnamic acid methoxycinnamic acid, para 3-(4- methoxyphenyl)-2-propenoic acid 3-(4- methoxyphenyl)acrylic acid 3-(4- methoxyphenyl)prop-2-enoic acid 2- propenoic acid, 3-(4-methoxyphenyl)- PubMed: [Chemical constituents from the aerial part of Sibiraea angustata]. PubMed: Protective effect of p-methoxycinnamic acid, an active phenolic acid against 1,2-dimethylhydrazine-induced colon carcinogenesis: modulating biotransforming bacterial enzymes and xenobiotic metabolizing enzymes. PubMed: Eco-friendly methodology for efficient synthesis and scale-up of 2-ethylhexyl-p-methoxycinnamate using Rhizopus oryzae lipase and its biological evaluation. PubMed: Quantification of phenolic acids and their methylates, glucuronides, sulfates and lactones metabolites in human plasma by LC-MS/MS after oral ingestion of soluble coffee. PubMed: Effects of four commonly used UV filters on the growth, cell viability and oxidative stress responses of the Tetrahymena thermophila. PubMed: Quantitative determination of phenolic compounds by UHPLC-UV-MS and use of partial least-square discriminant analysis to differentiate chemo-types of Chamomile/Chrysanthemum flower heads. PubMed: In vitro evaluation of caffeoyl and cinnamoyl derivatives as potential prolyl oligopeptidase inhibitors. PubMed: Anticholinesterase activity of phenolic acids and their derivatives. PubMed: Four new antioxidant phenylpropanoid glycosides from Microlepia pilosissima. PubMed: Potential antiarrhythmic effect of methyl 3,4,5-trimethoxycinnamate, a bioactive substance from roots of polygalae radix: suppression of triggered activities in rabbit myocytes. PubMed: New flavane gallates isolated from the leaves of Plicosepalus curviflorus and their hypoglycemic activity. PubMed: The modulatory influence of p-methoxycinnamic acid, an active rice bran phenolic acid, against 1,2-dimethylhydrazine-induced lipid peroxidation, antioxidant status and aberrant crypt foci in rat colon carcinogenesis. PubMed: Energetics and structural properties, in the gas phase, of trans-hydroxycinnamic acids. PubMed: Mechanisms of p-methoxycinnamic acid-induced increase in insulin secretion. PubMed: Evaluation of antioxidant activity of isoferulic acid in vitro. PubMed: Synthesis and evaluation of novel tetrapropoxycalix[4]arene enones and cinnamates for protection from ultraviolet radiation. PubMed: Chemical constituents of Polygala tenuifolia roots and their inhibitory activity on lipopolysaccharide-induced nitric oxide production in BV2 microglia. PubMed: Natural products modulate Shigella-host-cell interaction. PubMed: [Chemical constituents from aerial part of Atractylodes macrocephala]. PubMed: A comparison of skin delivery of ferulic acid and its derivatives: evaluation of their efficacy and safety. PubMed: The genome-wide expression profile of Scrophularia ningpoensis-treated thapsigargin-stimulated U-87MG cells. PubMed: [Studies on chemical constituents in roots and rhizomes of Notopterygium incisum]. PubMed: Insulin-releasing properties of a series of cinnamic acid derivatives in vitro and in vivo. PubMed: Glyceridic esters of p-methoxycinnamic acid. A new sunscreen of the cinnamate class. PubMed: Insulin-secretagogue activity of p-methoxycinnamic acid in rats, perfused rat pancreas and pancreatic beta-cell line. PubMed: 1-(1-Arylethylidene)thiosemicarbazide derivatives: a new class of tyrosinase inhibitors. PubMed: Antimicrobial phenolic derivatives from Dendranthema zawadskii var. latilobum Kitamura (Asteraceae). PubMed: Simultaneous determination of four active constituents in the roots of Scrophularia buergeriana by HPLC-DAD and LC-ESI-MS. PubMed: Production of stilbenoids and phenolic acids by the peanut plant at early stages of growth. PubMed: Enzymatic synthesis of cinnamic acid derivatives. PubMed: Synthesis and cosmetic whitening effect of glycosides derived from several phenylpropanoids. PubMed: Bioassay-guided isolation of a vasorelaxant active compound from Kaempferia galanga L. PubMed: Mechanisms of antihyperglycemic effect of p-methoxycinnamic acid in normal and streptozotocin-induced diabetic rats. PubMed: Ferulic acid dimer inhibits lipopolysaccharide-stimulated cyclooxygenase-2 expression in macrophages. PubMed: A new sunscreen of the cinnamate class: synthesis and enzymatic hydrolysis evaluation of glyceryl esters of p-methoxycinnamic acid. PubMed: Quantitative changes of secondary metabolites of Matricaria chamomilla by abiotic stress. PubMed: E- and Z-p-methoxycinnamic acid from Aquilegia vulgaris. PubMed: Spectroscopic evidence of silica-lignin complexes: implications for treatment of non-wood pulp wastewater. PubMed: Anti-amnestic activity of E-p-methoxycinnamic acid from Scrophularia buergeriana. PubMed: Cytotoxic and xenoestrogenic effects via biotransformation of trans-anethole on isolated rat hepatocytes and cultured MCF-7 human breast cancer cells. PubMed: Molecular markers of anthropogenic activity in sediments of the Havel and Spree Rivers (Germany). PubMed: Catalytic hunsdiecker reaction of alpha,beta-unsaturated carboxylic acids: how efficient is the catalyst? PubMed: A practical procedure for the large-scale preparation of methyl (2R,3S)-3-(4-methoxyphenyl)glycidate, a key intermediate for diltiazem. PubMed: Hepatoprotective phenylpropanoids from Scrophularia buergeriana roots against CCl(4)-induced toxicity: action mechanism and structure-activity relationship. PubMed: Photosensitive dermatitis due to sunscreen allergy in a child. PubMed: Tyrosinase inhibitors of Pulsatilla cernua root-derived materials. PubMed: E-p-methoxycinnamic acid protects cultured neuronal cells against neurotoxicity induced by glutamate. PubMed: Saponins-mediated potentiation of cisplatin accumulation and cytotoxicity in human colon cancer cells. PubMed: Selective growth inhibitor toward human intestinal bacteria derived from Pulsatilla cernua root. PubMed: Synthesis of 1,7-bis(4-hydroxypenyl)-4-hydroxy-1,3-heptadiene-5-one, an antiplatelet diarylheptanoid from Alpinia blepharocalyx K. schum. PubMed: Neuroprotective phenylpropanoid esters of rhamnose isolated from roots of Scrophularia buergeriana. PubMed: A strategy for the asymmetric aminohomologation of alpha, beta-dihydroxy aldehydes: application to the synthesis of the southwest tripeptide segment of echinocandin B. PubMed: Induction of histone acetylation and growth regulation in eryrthroleukemia cells by 4-phenylbutyrate and structural analogs. PubMed: Immunochemical identification of hepatic protein adducts derived from estragole. PubMed: Polyamine levels in various tissues of rats treated with 3-hydroxy-4-methoxycinnamic acid and 3,4-dimethoxycinnamic acid. PubMed: Studies on the constituents of Ailanthus integrifolia. PubMed: Oligosaccharide microscale analysis by circular dichroic spectroscopy: reference spectra for chromophoric D-fructofuranoside derivatives. PubMed: Determination of plasma homovanillic acid by liquid chromatography with electrochemical detection. PubMed: Phenylpropanoid Metabolism in Suspension Cultures of Vanilla planifolia Andr. : III. Conversion of 4-Methoxycinnamic Acids into 4-Hydroxybenzoic Acids. PubMed: Oligosaccharide microanalysis by c.d. spectroscopy. Reference curves for D-mannose derivatives. PubMed: Chronic actinic dermatitis. Study of the spectrum of chronic photosensitivity in 12 patients. PubMed: The changing role of ultraviolet spectroscopy in drug analysis. PubMed: Substantivity of sunscreens: an appraisal of some quaternary ammonium sunscreens. PubMed: Chloroperoxidase-catalyzed halogenation of trans-cinnamic acid and its derivatives. PubMed: [Biliary excretion of choleretically active cinnamic acid derivatives in the rat]. PubMed: Some properties of p-coumarate decarboxylase from Cladosporium phlei. PubMed: Synthesis and pharmacology of p-methoxycinnamic acid derivatives. PubMed: [Light protective effects of esters & amides of p-methoxycinnamic acid. 2. Light-protective effects of alkyl esters of p-methoxycinnamic acid & of p-acylamino- and alkoxyphenylacylpyridinium salts].