Ethyl cinnamate: Difference between revisions

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	{{~~Refimprove~~\|date=~~July~~ ~~2009~~}}		{{Use dmy dates\|date=August 2021}}
	{{chembox		{{chembox
			\| Watchedfields = changed
	\| verifiedrevid = ~~402114497~~		\| verifiedrevid = 407488762
	\| Name = Ethyl cinnamate		\| Name = Ethyl cinnamate
	\| ImageFile = ~~Ethyl_cinnamate~~.~~png~~		\| ImageFile = Ethyl-cinnamate.svg
	\| ImageSize = 200px		\| ImageSize = 200px
	\| ImageName = Skeletal formula
	\| ~~ImageFile1~~ = ~~Ethyl-~~cinnamate~~-3D-balls.png~~		\| ImageAlt = Skeletal formula of ethyl cinnamate
			\| ImageFile1 = Ethyl cinnamate 3D spacefill.png
	\| ImageSize1 = 210px		\| ImageSize1 = 210px
	\| ~~ImageName1~~ = Ball-and-stick model		\| ImageAlt1 = Ball-and-stick model of ethyl cinnamate
	\| ~~IUPACName~~ = Ethyl 3-phenylprop-2-enoate		\| PIN = Ethyl (2''E'')-3-phenylprop-2-enoate
⚫	\| Section1 = {{Chembox Identifiers
			\| OtherNames = Ethyl cinnamate
⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
		⚫	\|Section1={{Chembox Identifiers
		⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 553344		\| ChemSpiderID = 553344
	\| PubChem = 637758		\| PubChem = 637758
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	\| InChI = 1/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8+		\| InChI = 1/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8+
	\| InChIKey = KBEBGUQPQBELIU-CMDGGOBGBD		\| InChIKey = KBEBGUQPQBELIU-CMDGGOBGBD
			\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
			\| ChEMBL = 318196
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 1S/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8+		\| StdInChI = 1S/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8+
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	\| CASNo_Ref = {{cascite\|correct\|CAS}}		\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CASNo = 103-36-6		\| CASNo = 103-36-6
	\| SMILES = CCOC(=O)/C=C/c1ccccc1		\| SMILES = CCOC(=O)/C=C/c1ccccc1
	}}		}}
	\| Section2 = {{Chembox Properties		\|Section2={{Chembox Properties
	\| Formula = C<sub>11</sub>H<sub>12</sub>O<sub>2</sub>		\| Formula = C<sub>11</sub>H<sub>12</sub>O<sub>2</sub>
	\| MolarMass = 176.21 g/mol		\| MolarMass = 176.21 g/mol
	\| Density = 1.046 g/cm<sup>3</sup>		\| Density = 1.046 g/cm<sup>3</sup>
	\| ~~MeltingPt~~ = 6.5-8 °C		\| MeltingPtC = 6.5 to 8
	\| ~~BoilingPt~~ = 271 °C		\| BoilingPtC = 271
			\| MagSus = -107.5·10<sup>−6</sup> cm<sup>3</sup>/mol
	}}		}}
	}}		}}

	'''Ethyl cinnamate''' is the ] of ] and ]. It is present in the essential oil of ] {{Citation needed\|date=July 2009}}; ~~pure~~ ethyl cinnamate has a "fruity and balsamic odor, reminiscent of cinnamon with an amber note" <ref name="Merck-Index">{{cite journal \| author=Budavari, Susan \| title=Merck Index 13th Ed. \| journal=Merck & co., Inc \| year=2001}}</ref>.		'''Ethyl cinnamate''' is the ] of ] and ]. It is present in the essential oil of ].{{Citation needed\|date=July 2009}} Pure ethyl cinnamate has a "fruity and balsamic odor, reminiscent of cinnamon with an amber note".<ref name="Merck-Index">{{cite journal \| author=Budavari, Susan \| title=] 13th Ed. \| journal=Merck & Co., Inc \| year=2001}}</ref>

	~~<br/>~~The ''p''-methoxy ~~substitute~~ is reported to be a ]<ref name="Monoamine-oxidase-Noro">{{cite journal \| ~~author~~=Noro T, Miyase T, Kuroyanagi M, Ueno A, Fukushima S. \| title=Monoamine oxidase inhibitor from the rhizomes of Kaempferia galanga L. \| journal=Chem Pharm Bull ~~(Tokyo).~~ \| year=1983 \| pages=2708–11 \| volume=31 \| issue=8 \| pmid=6652816}}</ref>.		The ''p''-methoxy ] is reported to be a ].<ref name="Monoamine-oxidase-Noro">{{cite journal \|vauthors=Noro T, Miyase T, Kuroyanagi M, Ueno A, Fukushima S \| title=Monoamine oxidase inhibitor from the rhizomes of Kaempferia galanga L \| journal=Chem Pharm Bull \| year=1983 \| pages=2708–11 \| volume=31 \| issue=8 \| doi=10.1248/cpb.31.2708 \| pmid=6652816\| doi-access=free }}</ref> It can be synthesized by the esterification reaction involving ethanol and cinnamic acid in the presence of sulfuric acid.

	==List of plants that contain the chemical==		==List of plants that contain the chemical==
	* ] <ref name=ceor>{{cite journal		* '']''<ref name=ceor>{{cite journal
	\| ~~last~~ = Wong		\| last1 = Wong
	\| ~~first~~ = K. C. ~~''et al.''~~		\| first1 = K. C.
	\| authorlink =		\| authorlink =
		⚫	\| title = Composition of the essential oil of rhizomes of kaempferia galanga L
	\| coauthors =
⚫	\| title = ~~Compositon~~ of the essential oil of rhizomes of kaempferia galanga L.
	\| journal = Flavour and Fragrance Journal		\| journal = Flavour and Fragrance Journal
	\| volume = 7		\| volume = 7
	\| issue = 5		\| issue = 5
	\| pages = 263–266		\| pages = 263–266
	\| ~~publisher~~ =		\| year = 2006
	\| location =
⚫	\| ~~date~~ = ~~2006~~
	\| url =		\| url =
	\| issn =		\| issn =
	\| doi = 10.1002/ffj.2730070506		\| doi = 10.1002/ffj.2730070506
	\| id =		\| id =
	\| accessdate = 2 July 2009
	\| last2 = Ong		\| last2 = Ong
	\| first2 = K. S.		\| first2 = K. S.
	\| last3 = Lim		\| last3 = Lim
	\| first3 = C. L.~~}}</ref><sup>,</sup> <ref name=biva>{{cite journal~~		\| first3 = C. L.
			\| display-authors = 1}}</ref><ref name=biva>{{cite journal
	\| last = Othman
	\| ~~first~~ = ~~R. ''et al.''~~		\| last1 = Othman
		⚫	\| first1 = R.
	\| authorlink =		\| authorlink =
		⚫	\| title = Bioassay-guided isolation of a vasorelaxant active compound from Kaempferia galanga L
	\| coauthors =
⚫	\| title = Bioassay-guided isolation of a vasorelaxant active compound from Kaempferia galanga L.
	\| journal = Phytomedicine		\| journal = Phytomedicine
	\| volume = 13		\| volume = 13
	\| issue = ~~1 - 2~~		\| issue = 1–2
	\| pages = 61–66		\| pages = 61–66
	\| ~~publisher~~ =		\| year = 2006
	\| location =
	\| date = 2006
	\| url =		\| url =
	\| issn =		\| issn =
	\| doi = 10.1016/j.phymed.2004.07.004		\| doi = 10.1016/j.phymed.2004.07.004
	\| id =		\| id =
	\| accessdate = 2 July 2009
	\| pmid = 16360934		\| pmid = 16360934
	\| last2 = Ibrahim		\| last2 = Ibrahim
Line 86:		Line 85:
	\| first4 = MR		\| first4 = MR
	\| last5 = Awang		\| last5 = Awang
	\| first5 = K~~}}</ref>~~		\| first5 = K
			\| display-authors = 1}}</ref>

	==~~Toxicology~~==		== References ==
			{{reflist}}
	{{Empty section\|date=September 2009}}

	==Notes and references==
	{{Citation style\|date=September 2007}}
	<div style="font-size:88%;">
	<references />
	</div>

	{{Use dmy dates\|date=January 2011}}

	{{DEFAULTSORT:Ethyl Cinnamate}}		{{DEFAULTSORT:Ethyl Cinnamate}}
	]		]
	]		]
	]		]
	]		]
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	{{ester-stub}}		{{ester-stub}}

	]
	]
	]

Latest revision as of 14:21, 16 August 2021

Ethyl cinnamate
Names


Preferred IUPAC name Ethyl (2E)-3-phenylprop-2-enoate
Other names Ethyl cinnamate
Identifiers
CAS Number	103-36-6
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL318196
ChemSpider	553344
ECHA InfoCard	100.002.822
PubChem CID	637758
UNII	C023P3M5JJ
CompTox Dashboard (EPA)	DTXSID601017688 DTXSID9022520, DTXSID601017688
InChI InChI=1S/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8+Key: KBEBGUQPQBELIU-CMDGGOBGSA-N InChI=1/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8+Key: KBEBGUQPQBELIU-CMDGGOBGBD
SMILES CCOC(=O)/C=C/c1ccccc1
Properties
Chemical formula	C₁₁H₁₂O₂
Molar mass	176.21 g/mol
Density	1.046 g/cm
Melting point	6.5 to 8 °C (43.7 to 46.4 °F; 279.6 to 281.1 K)
Boiling point	271 °C (520 °F; 544 K)
Magnetic susceptibility (χ)	-107.5·10 cm/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

Ethyl cinnamate is the ester of cinnamic acid and ethanol. It is present in the essential oil of cinnamon. Pure ethyl cinnamate has a "fruity and balsamic odor, reminiscent of cinnamon with an amber note".

The p-methoxy derivative is reported to be a monoamine oxidase inhibitor. It can be synthesized by the esterification reaction involving ethanol and cinnamic acid in the presence of sulfuric acid.

List of plants that contain the chemical

Kaempferia galanga

References

Budavari, Susan (2001). "Merck Index 13th Ed". Merck & Co., Inc.
Noro T, Miyase T, Kuroyanagi M, Ueno A, Fukushima S (1983). "Monoamine oxidase inhibitor from the rhizomes of Kaempferia galanga L". Chem Pharm Bull. 31 (8): 2708–11. doi:10.1248/cpb.31.2708. PMID 6652816.
Wong, K. C.; et al. (2006). "Composition of the essential oil of rhizomes of kaempferia galanga L". Flavour and Fragrance Journal. 7 (5): 263–266. doi:10.1002/ffj.2730070506.
Othman, R.; et al. (2006). "Bioassay-guided isolation of a vasorelaxant active compound from Kaempferia galanga L". Phytomedicine. 13 (1–2): 61–66. doi:10.1016/j.phymed.2004.07.004. PMID 16360934.

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