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cinnamyl acetate

Chemical Structure

General Material Information

Preferred name cinnamyl acetate
Trivial Name Cinnamyl acetate
Short Description 3-phenyl-2-propen-1-yl acetate
Formula C11 H12 O2
CAS Number 103-54-8
FEMA Number 2293
ECHA Number 203-121-9
FDA UNII Search
Beilstein Number 2046000
MDL MFCD00008722
COE Number 208
xLogP3-AA 2.30 (est)
NMR Predictor External link
JECFA Food Flavoring 650 cinnamyl acetate
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 103-54-8 ; CINNAMYL ACETATE
Synonyms
  • acetic acid cinnamyl ester
  • 1-acetoxy-3-phenyl-2-propene
  • nat. cinnamyl acetate
  • cinnamyl acetate FCC
  • cinnamyl acetate natural
  • cinnamyl alcohol acetate
  • cinnamyln acetate
  • 3-phenyl allyl acetate
  • gamma- phenyl allyl acetate
  • 3-phenyl-2-propen-1-ol acetate
  • 3-phenyl-2-propen-1-yl acetate
  • 3-phenyl-2-propenyl acetate
  • 3-phenylprop-2-en-1-yl acetate
  • 3-phenylprop-2-enyl acetate
  • 2-propen-1-ol, 3-phenyl-, acetate
  • 3-phenylprop-2-enyl acetate
  • 2-Propen-1-ol, 3-phenyl-, 1-acetate
  • Cinnamyl alcohol, acetate
  • 2-Propen-1-ol, 3-phenyl-, acetate
  • γ-Phenylallyl acetate
  • 3-Phenyl-2-propen-1-yl acetate
  • 3-Phenyl-2-propenyl acetate
  • 3-Phenylallyl acetate
  • 1-Acetoxy-3-phenyl-2-propene
  • 3-Phenyl-2-propen-1-ol acetate
  • NSC 46109
  • Acetic acid 3-phenyl-2-propenyl ester

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

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Perfumer & Flavorists Start search
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Literature & References

3-phenylprop-2-enyl acetate
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:103-54-8
Pubchem (cid):7660
Pubchem (sid):134972232
Pherobase:View
Publications by PubMed
Controlled delivery of a new broad spectrum antibacterial agent against colitis: In vitro and in vivo performance.
Ultrasound assisted lipase catalyzed synthesis of cinnamyl acetate via transesterification reaction in a solvent free medium.
Commercial Origanum compactum Benth. and Cinnamomum zeylanicum Blume essential oils against natural mycoflora in Valencia rice.
Medicinal plants from the genus Acalypha (Euphorbiaceae)--a review of their ethnopharmacology and phytochemistry.
Key volatile aroma compounds of three black velvet tamarind (Dialium) fruit species.
Chemical composition of essential oils from four Vietnamese species of piper (piperaceae).
Asymmetric synthesis of α-allyl-α-aryl α-amino acids by tandem alkylation/π-allylation of α-iminoesters.
Cassia cinnamon as a source of coumarin in cinnamon-flavored food and food supplements in the United States.
Cinnamyl acetate synthesis by lipase-catalyzed transesterification in a solvent-free system.
Synthesis of diphenylhexatriene by the Pd-catalyzed dimerization of cinnamyl acetate.
Structural analysis of the alcohol acyltransferase protein family from Cucumis melo shows that enzyme activity depends on an essential solvent channel.
Chemistry, biogenesis, and biological activities of Cinnamomum zeylanicum.
Terpenoid composition and antifungal activity of three commercially important essential oils against Aspergillus flavus and Aspergillus niger.
Contact and fumigant toxicity of cinnamaldehyde and cinnamic acid and related compounds to Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae).
Characterization of odor-active compounds in guava wine.
Composition, antimicrobial activity and in vitro cytotoxicity of essential oil from Cinnamomum zeylanicum Blume (Lauraceae).
A novel hemilabile calix[4],quinoline-based P,N-ligand: coordination chemistry and complex characterisation.
Molecular-weight-enlarged multiple-pincer ligands: synthesis and application in palladium-catalyzed allylic substitution reactions.
Characterization of the key aroma compounds in pink guava (Psidium guajava L.) by means of aroma re-engineering experiments and omission tests.
Characterization of the aroma-active compounds in pink guava (Psidium guajava, L.) by application of the aroma extract dilution analysis.
Insecticidal activities of leaf essential oils from Cinnamomum osmophloeum against three mosquito species.
Fragrance material review on cinnamyl acetate.
Structure and reaction mechanism of basil eugenol synthase.
Anti-inflammation activities of essential oil and its constituents from indigenous cinnamon (Cinnamomum osmophloeum) twigs.
Acaricidal activities of paeonol and benzoic acid from Paeonia suffruticosa root bark and monoterpenoids against Tyrophagus putrescentiae (Acari: Acaridae).
Ovicidal and adulticidal activities of Cinnamomum zeylanicum bark essential oil compounds and related compounds against Pediculus humanus capitis (Anoplura: Pediculicidae).
Chemical polymorphism and antifungal activity of essential oils from leaves of different provenances of indigenous cinnamon (Cinnamomum osmophloeum).
Essential oil yield and quality of methyl eugenol rich Ocimum tenuiflorum L.f. (syn. O. sanctum L.) grown in south India as influenced by method of harvest.
Optimization of a chemical attractant for Epicometis (Tropinota) hirta Poda.
Chemical composition and mosquito larvicidal activity of essential oils from leaves of different Cinnamomum osmophloeum provenances.
Control of diastereoselectivity in the crotylation and cinnamylation of aldehydes by the selection of ligands on allylic indium reagents.
Volatile constituents from Cinnamomum zeylanicum fruit stalks and their antioxidant activities.
Asymmetric allylation of unsymmetrical 1,3-diketones using a BINAP-palladium catalyst.
Constituents of the essential oil of the Cinnamomum cassia stem bark and the biological properties.
Essential oils from Azorean Laurus azorica.
Chemical composition of the flower oil of Cinnamomum zeylanicum blume.
Kinetic analysis of the chloride dependence of the neuronal uptake of dopamine and effect of anions on the ability of substrates to compete with the binding of the dopamine uptake inhibitor GBR 12783.
Composition of essential oils of Laurus nobilis, L. nobilis var. angustifolia and Laurus azorica.

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
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C12299
HMDB (The Human Metabolome Database):HMDB29699
FooDB:FDB000889
Export Tariff Code:2916.39.7900
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 176.21504211426
Specific gravity @ 25 °C
Pounds per Gallon 8.72 to 8.787
Specific gravity @ 20 °C
Pounds per Gallon 8.739 to 8.806
Refractive Index 1.539 to 1.544 @ 20 °C
Boiling Point 262 to 265°C @ 760 mm Hg
Acid Value 1 max KOH/g
Vapor Pressure 0.011 mmHg @ 20 °C
Flash Point TCC Value 100 °C TCC
logP (o/w) 2.641 est
Shelf life 24 months (or longer if stored properly.)
Storage notes Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
alcohol Yes
fixed oils Yes
water, 334 mg/L @ 20 °C (exp) Yes
water No
glycerin No
Stability
bath foam Unspecified
cream Unspecified
detergent Unspecified
hair spray Unspecified
lotion Unspecified
non-discoloring Unspecified
powder Unspecified
soap Unspecified

Organoleptic Properties

Odor Type: Spicy
sweet, floral, spicy, balsamic, cinnamon, estery, powdery, rose
Odor strength medium
Substantivity 124 hour(s) at 100.00 %
Luebke, William tgsc, (1982) At 100.00 %. sweet floral spicy balsam cinnamon
Mosciano, Gerard P&F 23, No. 2, 43, (1998) Sweet, floral, cinnamon, spicy, estery and powdery with a rosy nuance
Flavor Type: Spicy
sweet, spicy, floral, cinnamon, honey, tutti frutti
Mosciano, Gerard P&F 23, No. 2, 43, (1998) At 15.00 ppm. Sweet, spicy, floral, cinnamon and honey with a tutti-fruti nuance
Useful in: brown cocoa, brown others, fruity red, fruity yellow, fruity tropical, fruity others, sweet others. Cinnamon, chocolate, vanilla, fatty, oily
General comment Sweet aromatic, cinnamon, chocolate, vanilla, fatty, oily

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36 - Irritating to eyes.
S 02 - Keep out of the reach of children.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 37/39 - Wear suitable gloves and eye/face protection.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Eye irritation (Category 2A), H319
GHS Label elements, including precautionary statements
Pictogramexclamation-mark.jpg
Signal word Warning
Hazard statement(s)
H319 - Causes serious eye irritation
Precautionary statement(s)
P264 - Wash skin thouroughly after handling.
P280 - Wear protective gloves/protective clothing/eye protection/face protection.
P305 + P351 + P338 - IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P337 + P313 - IF eye irritation persists: Get medical advice/attention.
Human Experience:
5 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 3300 mg/kg
Food and Cosmetics Toxicology. Vol. 11, Pg. 1063, 1973.

oral-guinea pig LD50 4750 mg/kg
Voprosy Pitaniya. Problems of Nutrition. Vol. 33(5), Pg. 48, 1974.

intraperitoneal-mouse LD50 1200 mg/kg
Pharmacologist. Vol. 3, Pg. 62, 1961.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 11, Pg. 1063, 1973.

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
limits in the finished product for - "leave on the skin contact":
0.6200 % Restriction.
Recommendation for cinnamyl acetate usage levels up to:
8.0000 % in the fragrance concentrate.
use level in formulae for use in cosmetics:
0.4530 %
Dermal Systemic Exposure in Cosmetic Products:
0.0115 mg/kg/day (IFRA, 2001)
Maximised Survey-derived Daily Intakes (MSDI-EU): 180.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 300.00 (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: -11.00000
beverages(nonalcoholic): -2.70000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: -8.70000
condiments / relishes: 2.000002.00000
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -6.50000
fruit ices: -6.50000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -16.00000
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):

Flavouring Group Evaluation 214: alpha,beta-Unsaturated aldehydes and precursors from chemical subgroup 3.1 of FGE.19: Cinnamyl derivatives[1]
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):103-54-8
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7660
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
3-phenylprop-2-enyl acetate
Chemidplus:0000103548
RTECS:GE2275000 for cas# 103-54-8