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methyl cinnamate

Chemical Structure

General Material Information

Preferred name methyl cinnamate
Trivial Name Methyl cinnamate
Short Description cinnamic acid methyl ester
Formula C10 H10 O2
CAS Number 103-26-4
FEMA Number 2698
Flavis Number 9.74
ECHA Number 203-093-8
FDA UNII 533CV2ZCQL
Beilstein Number 0386468
MDL MFCD00008458
COE Number 333
NMR Predictor External link
JECFA Food Flavoring 658 methyl cinnamate
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 103-26-4 ; METHYL CINNAMATE
Synonyms
  • 3-phenyl-2-propenoic acid methyl ester
  • cinnamic acid methyl ester
  • methyl 3-phenyl acrylate
  • methyl 3-phenyl propenoate
  • methyl 3-phenyl-2-propenoate
  • methyl 3-phenylprop-2-enoate
  • methyl cinnamate FCC
  • methyl cinnamate FCC (natural)
  • methyl cinnamate nat.
  • methyl cinnamate natural
  • methyl cinnamylate
  • nat. methyl cinnamate
  • methyl 3-phenylprop-2-enoate
  • 2-Propenoic acid, 3-phenyl-, methyl ester
  • Cinnamic acid, methyl ester
  • Methyl 3-phenylpropenoate
  • Methyl 3-phenylacrylate
  • 3-Phenyl-2-propenoic acid methyl ester
  • 3-Phenylacrylic acid methyl ester
  • NSC 9411
  • SemaSORB 9815

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

methyl 3-phenylprop-2-enoate
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:103-26-4
Pubchem (cid):7644
Pubchem (sid):134971915
Flavornet:103-26-4
Pherobase:View
Publications by Info
Volatile Flavor Components in Bogyojosaeng and Suhong Cultivars of Strawberry (Fragaria ananassa Duch.)
Publications by PubMed
Chemical Diversity in Basil (Ocimum sp.) Germplasm.
A DFT Study of the Photochemical Dimerization of Methyl 3-(2-Furyl)acrylate and Allyl Urocanate.
Identification and Quantification of Several Contaminated Compounds in Replacement Liquids of Electronic Cigarettes by Gas Chromatography-Mass Spectrometry.
Identification of volatiles in leaves of Alpinia zerumbet 'Variegata' using headspace solid-phase microextraction-gas chromatography-mass spectrometry.
Mikania glomerata: Phytochemical, Pharmacological, and Neurochemical Study.
Vasorelaxation induced by methyl cinnamate, the major constituent of the essential oil of Ocimum micranthum, in rat isolated aorta.
Antispasmodic and myorelaxant effects of the flavoring agent methyl cinnamate in gut: potential inhibition of tyrosine kinase.
Hydroxylated HMPA enhances both reduction potential and proton donation in SmI₂ reactions.
Optimization of antimicrobial and physical properties of alginate coatings containing carvacrol and methyl cinnamate for strawberry application.
Pharmacokinetic study of cinnamaldehyde in rats by GC-MS after oral and intravenous administration.
Formation of complex natural flavours by biotransformation of apple pomace with basidiomycetes.
Antinociceptive and antispasmodic effects of the essential oil of Ocimum micranthum: potential anti-inflammatory properties.
Methyl cinnamate inhibits adipocyte differentiation via activation of the CaMKK2-AMPK pathway in 3T3-L1 preadipocytes.
Chemical and biological diversity in fourteen selections of four Ocimum species.
Quantification of character-impacting compounds in Ocimum basilicum and 'Pesto alla Genovese' with selected ion flow tube mass spectrometry.
Safety assessment of Zanthoxylum alatum Roxb. essential oil, its antifungal, antiaflatoxin, antioxidant activity and efficacy as antimicrobial in preservation of Piper nigrum L. fruits.
BF3·OEt2-promoted diastereoselective diacetoxylation of alkenes by PhI(OAc)2.
Chemical composition of the essential oil from basil (Ocimum basilicum Linn.) and its in vitro cytotoxicity against HeLa and HEp-2 human cancer cell lines and NIH 3T3 mouse embryonic fibroblasts.
Identification of mosquito repellent odours from Ocimum forskolei.
Optimization and Validation of RP-HPLC-UV/Vis Method for Determination Phenolic Compounds in Several Personal Care Products.
A succinct synthesis of the vaulted biaryl ligand vanol via a dienone-phenol rearrangement.
Chemical characterization and antimicrobial activity of rhizome essential oils of very closely allied Zingiberaceae species endemic to Borneo: Alpinia ligulata K. Schum. and Alpinia nieuwenhuizii Val.
cis-Dihydroxylation of alkenes with oxone catalyzed by iron complexes of a macrocyclic tetraaza ligand and reaction mechanism by ESI-MS spectrometry and DFT calculations.
Chemical diversity in the genus Alpinia (Zingiberaceae): comparative composition of four Alpinia species grown in Northern India.
Enhanced repellency of binary mixtures of Zanthoxylum piperitum pericarp steam distillate or Zanthoxylum armatum seed oil constituents and Calophyllum inophyllum nut oil and their aerosols to Stomoxys calcitrans.
Ocotea quixos Lam. essential oil: in vitro and in vivo investigation on its anti-inflammatory properties.
Production and biochemical characterization of a type B ferulic acid esterase from Streptomyces ambofaciens.
Identification of the constituents of balsam of peru in tomatoes.
Inhibitory effects of methyl trans-cinnamate on mushroom tyrosinase and its antimicrobial activities.
Total synthesis of the potent anticancer Aglaia metabolites (-)-silvestrol and (-)-episilvestrol and the active analogue (-)-4'-desmethoxyepisilvestrol.
Composition and seasonal variation of essential oil in Alpinia zerumbet from Okinawa Island.
Yield and oil composition of 38 basil (Ocimum basilicum L.) accessions grown in Mississippi.
Tricholoma matsutake 1-Ocen-3-ol and methyl cinnamate repel mycophagous Proisotoma minuta (Collembola: Insecta).
Fragrance material review on methyl cinnamate.
25 years of natural product R&D with New South Wales agriculture.
Nematicidal Activity of Cassia and Cinnamon Oil Compounds and Related Compounds toward Bursaphelenchus xylophilus (Nematoda: Parasitaphelenchidae).
Composition of the essential oils of Ocimum canum, O. gratissimum and O. minimum.
Density functional theory study of electroreductive hydrocoupling of alpha,beta-unsaturated carbonyl compounds.
Antiplatelet and antithrombotic activities of essential oil from wild Ocotea quixos (Lam.) Kosterm. (Lauraceae) calices from Amazonian Ecuador.
Cinnamate metabolism in ripening fruit. Characterization of a UDP-glucose:cinnamate glucosyltransferase from strawberry.
Stable isotope characterization of the ortho-oxygenated phenylpropanoids: coumarin and melilotol.
Evaluation of the main contact allergens in propolis (1995 to 2005).
IP3 production in the hypersensitive response of lemon seedlings against Alternaria alternata involves active protein tyrosine kinases but not a G-protein.
Effect of cyclodextrin complexation in bromine addition to unsymmetrical olefins: evidence for participation of cyclodextrin hydroxyl groups.
Natural product propolis: chemical composition.
Differences in the volatile components and their odor characteristics of green and ripe fruits and dried pericarp of Japanese pepper (Xanthoxylum piperitum DC.).
Essential oils from New Zealand manuka: triketone and other chemotypes of Leptospermum scoparium.
Determination of 2H/1H and 13C/12C isotope ratios of (E)-methyl cinnamate from different sources using isotope ratio mass spectrometry.
Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from southern India.
Odor compound detection in male euglossine bees.
Synthesis and evaluation of anti-HIV-1 and anti-HSV-1 activities of 4H-[1,2,4]-triazolo[1,5-a]pyrimidin-5-one derivatives.
Unusual Regioselectivity of the Dipolar Cycloaddition Reactions of Nitrile Oxides and Tertiary Cinnamides and Crotonamides(1).
Investigations in the transition metal catalyzed aziridination of olefins, amination, and other insertion reactions with Bromamine-T as the source of nitrene.
Influence of packaging on the aroma stability of strawberry syrup during shelf life.
Structure-antimutagenic activity relationships of benzalacetone derivatives against UV-induced mutagenesis in E. coli WP2uvrA and gamma-induced mutagenesis in Salmonella typhimurium TA2638.
[Phytochemical study of liverworts Conocephalum conicum and Chiloscyphus polyanthos].
Influence of plant growth stage on the essential oil content and composition in Davana (Artemisia pallens wall.).
Enhanced benzaldehyde formation by a monokaryotic strain of Pycnoporus cinnabarinus using a selective solid adsorbent in the culture medium.
Catalytic asymmetric aminohydroxylation provides a short taxol side-chain synthesis.
Inhibition of human immunodeficiency virus type-1 integrase by curcumin.
Protein tyrosine kinase inhibitors inhibit chemotaxis of vascular smooth muscle cells.
Propolis allergy (IV). Studies with further sensitizers from propolis and constituents common to propolis, poplar buds and balsam of Peru.
The potency of inducers of NAD(P)H:(quinone-acceptor) oxidoreductase parallels their efficiency as substrates for glutathione transferases. Structural and electronic correlations.
Composition of the essential oil of Ocimum canum grown in Rwanda.
Methyl cinnamate derivatives enhance UV-induced mutagenesis due to the inhibition of DNA excision repair in Escherichia coli B/r.
Thermodynamic parameters of molecular complexes in aqueous solution: enthalpy-entropy compensation in a series of complexes of caffeine with beta- naphthoxyacetic acid and drug-related aromatic compounds.
Isolation and identification of mercapturic acid metabolites of phenyl substituted acrylate esters from urine of female rats.
Ocotea quixos, American cinnamon.
Stoichiometric model of alpha-cyclodextrin complex formation.
The absorption and metabolism of methyl cinnamate.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEMBL:View
KEGG (GenomeNet):C06358
HMDB (The Human Metabolome Database):HMDB33833
FooDB:FDB012001
YMDB (Yeast Metabolome Database):YMDB01744
Export Tariff Code:2916.39.7900
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

Suppliers

ACS International Advanced Biotech
Alfrebro Ambles Nature et Chimie
Anhui Haibei Apple Flavor & Fragrance
Astral Extracts Augustus Oils
Aurochemicals Axxence Aromatic
Beijing Lys Chemicals Berjé
BOC Sciences Charkit Chemical
Citrus and Allied Essences Creatingperfume.com
De Monchy Aromatics Ernesto Ventós
Excellentia International ExtraSynthese
Fleurchem Foreverest Resources
Global Essence H. Interdonati, Inc.
Indenta Group Indukern F&F
Jiangyin Healthway K.L. Koh Enterprise
Keva Kun Shan P&A
Lluch Essence M&U International
Moellhausen Nagar Haveli Perfumes & Aromatics
Natural Advantage Naturamole
O'Laughlin Industries Odowell Co.,ltd
Pearlchem Corporation Pell Wall Perfumes
Penta International PerfumersWorld
Perfumery Laboratory Phoenix Aromas & Essential Oils
Prodasynth PT Mitra Ayu Adi Pratama
R C Treatt & Co Ltd Reincke & Fichtner
Riverside Aromatics Robertet
Sigma-Aldrich SRS Aromatics
Sunaux International Symrise
Taytonn ASCC TCI AMERICA
Tengzhou Xiang Yuan Aroma Chemicals The John D. Walsh Company
The Lermond Company The Perfumers Apprentice
U. K. Aromatics and Chemicals United International
Vigon International Vistachem
WholeChem ACS International GmbH
Advanced Biotech. Inc. Alfrebro LLC/ Archer Daniels Midland Company
Augustus Oils Ltd Axxence Aromatic GmbH
Beijing Lys Chemicals Co, LTD. Berje Inc.
Charkit Chemical Corporation Fleurchem, Inc.
Foreverest Resources Ltd. Global Essence Inc.
Indukern, S.A. F&F Ingredients Division Jiangyin Healthway International Trade Co., Ltd
Lluch Essence S.L. M&U International LLC
Moellhausen S.P.A. O'Laughlin Industries Inc.
Penta International Corporation PerfumersWorld Ltd.
Riverside Aromatics Ltd. Robertet, Inc.
SRS Aromatics Ltd Symrise AG
Taytonn ASCC Pte Ltd The John D. Walsh Company, Inc
R C Treatt and Co Ltd Qingdao Free Trade Zone United International Co Ltd
Ernesto Ventós S.A. WholeChem, LLC

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 162.18809509277
Boiling Point 260 to 262°C @ 760 mm Hg
Boiling Point 164 to 165°C @ 50 mm Hg
Acid Value 2 max KOH/g
Vapor Pressure 0.011 mmHg @ 25 °C
Flash Point TCC Value 141.11 °C TCC
logP (o/w) 2.62
Solubility
alcohol Yes
dipropylene glycol Yes
fixed oils Yes
paraffin oil Yes
water, 387.1 mg/L @ 25 °C (est) Yes
Stability
bath foam Unspecified
cream Unspecified
hair spray Unspecified
non-discoloring in most media Unspecified
powder Unspecified
shampoo Unspecified

Organoleptic Properties

Odor Type: Balsamic
sweet, balsamic, strawberry, cherry, cinnamyl
Odor strength medium
Substantivity 164 hour(s) at 100.00 %
Luebke, William tgsc, (1983) At 100.00 %. sweet balsam strawberry cherry cinnamon
Flavor Type: Spicy
cinnamyl, balsamic, spicy, fruity, mango, papaya, cherry
Luebke, William tgsc, (1983) Cinnamyl balsamic spicy fruity mango papaya cherry
Useful in: vanilla, fruity red, fruity yellow, fruity tropical. Cinnamon, sweet, balsamic, heavy-fruity, strawberry
General comment Sweet, strawberry

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Acute toxicity, Oral (Category 4), H302
GHS Label elements, including precautionary statements
Pictogramexclamation-mark.jpg
Signal word Warning
Hazard statement(s)
H302 - Harmful if swallowed
Precautionary statement(s)
P264 - Wash skin thouroughly after handling.
P270 - Do not eat, drink or smoke when using this product.
P301 + P312 - IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P330 - Rinse mouth.
P501 - Dispose of contents/ container to an approved waste disposal plant.
Human Experience:
10 % solution no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 [sex: M,F] 2610 mg/kg
Confidence limits of 2000-3410 mg/kg bw, 6 doses up to 6000 mg/kg bw) were given to groups of 5 M and 5 F.
(Wong & Weir, 1971b)

oral-rat LD50 2610 mg/kg
Food and Cosmetics Toxicology. Vol. 13, Pg. 849, 1975.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 13, Pg. 849, 1975.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
maximum skin levels for fine fragrances:
0.3100 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey).(IFRA, 2001)
Recommendation for methyl cinnamate usage levels up to:
8.0000 % in the fragrance concentrate.
use level in formulae for use in cosmetics:
0.2100 %
Dermal Systemic Exposure in Cosmetic Products:
0.0054 mg/kg/day (IFRA, 2001)
Maximised Survey-derived Daily Intakes (MSDI-EU): 2400.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 830.00 (μg/capita/day)
Structure Class: I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: -13.00000
beverages(nonalcoholic): -1.90000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: 2.7000040.00000
condiments / relishes: -0.40000
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -3.80000
fruit ices: -3.80000
gelatins / puddings: 1.7000014.00000
granulated sugar: --
gravies: --
hard candy: -8.70000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 15 (FGE.15): Aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives from chemical group 22 (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf

Flavouring Group Evaluation 55 (FGE.55): Consideration of phenyl-substituted aliphatic alcohols and related aldehydes and esters evaluated by JECFA (63rd meeting) structurally related to phenethyl alcohol, aldehyde, esters and related phenylacetic acid esters evaluated by EFSA in FGE.14 (2005) and aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives evaluated by EFSA in FGE.15 (2005) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 15, Revision 1 (FGE.15Rev1) - Aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives from chemical group 22 - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 68 (FGE.68): Consideration of cinnamyl alcohol and related flavouring agents evaluated by JECFA (55th meeting) evaluated by EFSA in FGE.15Rev1 (2008)
View page or View pdf

Safety and efficacy of aryl-substituted primary alcohol, aldehyde, acid, ester and acetal derivatives belonging to chemical group 22 when used as flavourings for all animal species
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):103-26-4
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7644
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
methyl 3-phenylprop-2-enoate
Chemidplus:0000103264
RTECS:GE0190000 for cas# 103-26-4