From Wikipedia, the free encyclopedia
Methyl cinnamate
[1]
[2]
Names
Preferred IUPAC name
Methyl (2E )-3-phenylprop-2-enoate
Other names
Methyl cinnamate
Identifiers
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.002.813
EC Number
KEGG
UNII
InChI=1S/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7+
N Key: CCRCUPLGCSFEDV-BQYQJAHWSA-N
N InChI=1/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7+
Key: CCRCUPLGCSFEDV-BQYQJAHWBN
Properties
C 10 H 10 O 2
Molar mass
162.188 g·mol−1
Density
1.092 g/cm3
Melting point
34–38 °C (93–100 °F; 307–311 K)
Boiling point
261–262 °C (502–504 °F; 534–535 K)
Insoluble
Hazards
GHS labelling :
[3]
Warning
H317
P261 ,
P272 ,
P280 ,
P302+P352 ,
P321 ,
P333+P313 ,
P363 ,
P501
Flash point
> 110 °C (230 °F; 383 K)
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Methyl cinnamate is the
methyl
ester of
cinnamic acid and is a white or transparent solid with a strong, aromatic odor. It is found naturally in a variety of plants, including in fruits, like
strawberry , and some culinary spices, such as
Sichuan pepper and some varieties of
basil .
[4]
Eucalyptus olida has the highest known concentrations of methyl cinnamate (98%) with a 2–6% fresh weight yield in the leaf and twigs.
[5]
Methyl cinnamate is used in the flavor and perfume industries. The flavor is fruity and strawberry-like; and the odor is sweet, balsamic with fruity odor, reminiscent of cinnamon and strawberry.
[1]
It is known to attract males of various
orchid bees , such as
Aglae caerulea .
[6]
Methyl cinnamate crystals extracted using steam distillation from Eucalyptus olida .
List of plants that contain the chemical
Eucalyptus olida 'Strawberry Gum'
Ocotea quixos South American (Ecuadorian) Cinnamon, Ishpingo
[7]
Ocimum americanum cv. Purple Lovingly (Querendona Morada)
Ocimum americanum cv. Purple Castle (Castilla Morada)
Ocimum americanum cv. Purple Long-legged (Zancona morada)
Ocimum americanum cv. Clove (Clavo)
Ocimum basilicum cv. Sweet Castle (Dulce de Castilla)
Ocimum basilicum cv. White Compact (Blanca compacta)
Ocimum basilicum cv. large green leaves (verde des horjas grandes )
Ocimum micranthum cv. Cinnamon (Canela)
Ocimum minimum cv. Little Virgin (Virgen pequena)
Ocimum minimum cv. Purple Virgin (Virgen morada)
Ocimum sp. cv. Purple ruffle (Crespa morada)
Ocimum sp. cv. White Ruffle (Crespa blanca)
Stanhopea embreei , an orchid
Vanilla
Toxicology and safety
Moderately toxic by ingestion. The oral
LD50 for rats is 2610 mg/kg.
[8]
It is combustible as a liquid, and when heated to decomposition it emits acrid smoke and irritating fumes.
Compendial status
See also
References
^
a
b
Methyl cinnamate , at goodscents.com
^
Methyl cinnamate , at Sigma-Aldrich
^
"Methyl cinnamate" . pubchem.ncbi.nlm.nih.gov .
^ Viña, Amparo; Murillo, Elizabeth (2003).
"Essential oil composition from twelve varieties of basil (Ocimum spp) grown in Colombia" . Journal of the Brazilian Chemical Society . 14 (5): 744–9.
doi :
10.1590/S0103-50532003000500008 .
^ Boland DJ, Brophy JJ, House APN (1991). Eucalyptus Leaf Oils .
ISBN
978-0-909605-69-8 .
^ Williams, N.H.; Whitten, W.M. (1983).
"Orchid floral fragrances and male euglossine bees: methods and advances in the last sesquidecade" . Biol. Bull . 164 (3): 355–395.
doi :
10.2307/1541248 .
JSTOR
1541248 .
^ Bruni, Renato; Medici, Alessandro; Andreotti, Elisa; Fantin, Carlo; Muzzoli, Mariavittoria; Dehesa, Marco; Romagnoli, Carlo; Sacchetti, Gianni (2004). "Chemical composition and biological activities of Ishpingo essential oil, a traditional Ecuadorian spice from Ocotea quixos (Lam.) Kosterm. (Lauraceae) flower calices". Food Chemistry . 85 (3): 415–21.
doi :
10.1016/j.foodchem.2003.07.019 .
hdl :
11381/1449234 .
^ Richard J. Lewis (1989).
Food Additives Handbook . Springer Science & Business Media. pp. 304–.
ISBN
978-0-442-20508-9 .
^
Therapeutic Goods Administration (1999).
"Approved Terminology for Medicines" (PDF) . Archived from
the original (PDF) on 22 May 2006. Retrieved 29 June 2009 .