- 関
- cinnamate
WordNet
- street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
- any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
- having the characteristics of an acid; "an acid reaction"
PrepTutorEJDIC
- 酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/02/07 08:11:34」(JST)
[Wiki en表示]
Cinnamic acid
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| Names |
Preferred IUPAC name
(2E)-3-Phenylprop-2-enoic acid
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Other names
Cinnamic acid
trans-Cinnamic acid
Phenylacrylic acid[1]
Cinnamylic acid
3-Phenylacrylic acid
(E)-Cinnamic acid
Benzenepropenoic acid
Isocinnamic acid |
| Identifiers |
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CAS Number
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140-10-3 Y |
| 3D model (Jmol) |
Interactive image |
| ChEBI |
CHEBI:35697 Y |
| ChEMBL |
ChEMBL27246 Y |
| ChemSpider |
392447 Y |
| ECHA InfoCard |
100.004.908 |
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IUPHAR/BPS
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3203 |
| KEGG |
C00423 Y |
| PubChem |
444539 |
| UNII |
U14A832J8D N |
InChI
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InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+ Y
Key: WBYWAXJHAXSJNI-VOTSOKGWSA-N Y
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InChI=1/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
Key: WBYWAXJHAXSJNI-VOTSOKGWBT
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| Properties |
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Chemical formula
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C9H8O2 |
| Molar mass |
148.16 g·mol−1 |
| Appearance |
White monoclinic crystals |
| Density |
1.2475 g/cm3[2] |
| Melting point |
133 °C (271 °F; 406 K)[2] |
| Boiling point |
300 °C (572 °F; 573 K)[2] |
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Solubility in water
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500 mg/L[2] |
| Acidity (pKa) |
4.44 |
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Magnetic susceptibility (χ)
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-78.36·10−6 cm3/mol |
| Hazards |
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EU classification (DSD)
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Irritant (Xi) |
| R-phrases |
R36 |
| S-phrases |
S25 |
| NFPA 704 |
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| Flash point |
> 100 °C (212 °F; 373 K)[2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| N verify (what is YN ?) |
| Infobox references |
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Cinnamic acid is an organic compound with the formula C6H5CHCHCO2H. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents.[3] Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common.[4]
Contents
- 1 Occurrence and production
- 1.1 Natural occurrence
- 1.2 Production
- 2 Uses
- 3 References
Occurrence and production
Natural occurrence
It is obtained from oil of cinnamon, or from balsams such as storax.[5] It is also found in shea butter. Cinnamic acid has a honey-like odor;[6] it and its more volatile ethyl ester (ethyl cinnamate) are flavor components in the essential oil of cinnamon, in which related cinnamaldehyde is the major constituent. Cinnamic acid is also part of the biosynthetic shikimate and phenylpropanoid pathways. Its biosynthesis is performed by action of the enzyme phenylalanine ammonia-lyase (PAL) on phenylalanine.
Production
The original synthesis of cinnamic acid involves the Perkin reaction, which entails the base-catalysed condensation of acetic anhydride and benzaldehyde. Rainer Ludwig Claisen (1851–1930) described the synthesis of cinnamate esters by the reaction of benzaldehyde and esters.[7] The reaction is known as the Aldol condensation (with accompanying hydrolysis of the anhydride). It can also be prepared from cinnamaldehyde and benzal chloride.[4]
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Synthesis of cinnamic acid via Perkin reaction
Uses
Cinnamic acid is used in flavors, synthetic indigo, and certain pharmaceuticals. A major use is in the manufacturing of the methyl, ethyl, and benzyl esters for the perfume industry.[5] Cinnamic acid is a precursor to the sweetener aspartame via enzyme-catalysed amination to phenylalanine.[4] Cinnamic acid can dimerize in non-polar solvents resulting in different linear free energy relationships[8]
References
- ^ "Cinnamic Acid". Encyclopædia Britannica. 6 (11th ed.). 1911. p. 376.
- ^ a b c d e Record in the GESTIS Substance Database of the IFA
- ^ "Open Notebook Science Challenge: Solubilities of Organic Compounds in Organic Solvents". Nature Precedings. 2010. doi:10.1038/npre.2010.4243.3.
- ^ a b c Dorothea Garbe "Cinnamic Acid" in Ullmann's Encyclopedia of Industrial Chemistry, 2000, Wiley-VCH, Weinheim. doi:10.1002/14356007.a07_099
- ^ a b Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123
- ^ Cinnamic acid, flavornet.org
- ^ Claisen, L. (1890) "Zur Darstellung der Zimmtsäure und ihrer Homologen" (On the preparation of cinnamic acid and its homologues), Berichte der deutschen chemischen Gesellschaft, 23 : 976–978.
- ^ J-C Bradley et al., “Determination of Abraham model solute descriptors for the monomeric and dimeric forms of trans-cinnamic acid using measured solubilities from the Open Notebook Science Challenge”, Chemistry Central Journal 9:11 (2015)
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Types of hydroxycinnamic acids
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| Aglycones |
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Precursor
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Monohydroxycinnamic acids
(Coumaric acids)
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- p-Coumaric acid
- o-Coumaric acid
- m-Coumaric acid
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Dihydroxycinnamic acids
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- Caffeic acid (3,4-dihydroxycinnamic acid)
- Umbellic acid (2,4-dihydroxycinnamic acid)
- 2,3-Dihydroxycinnamic acid
- 2,5-Dihydroxycinnamic acid
- 3,5-Dihydroxycinnamic acid
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Trihydroxycinnamic acids
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- 2,4,5-Trihydroxycinnamic acid
- 3,4,5-Trihydroxycinnamic acid
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O-methylated forms
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- Ferulic acid
- 5-Hydroxyferulic acid
- Isoferulic acid
- Sinapinic acid
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others
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| Esters |
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glycoside-likes
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Esters of
caffeic acid
with cyclitols |
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esters of
quinic acid
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- Chlorogenic acid (3-caffeoylquinic acid)
- Cryptochlorogenic acid (4-O-caffeoylquinic acid)
- Neochlorogenic acid (5-O-Caffeoylquinic acid)
- Cynarine (1,5-dicaffeoylquinic acid)
- 3,4-dicaffeoylquinic acid
- 3,5-dicaffeoylquinic acid
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esters of
shikimic acid
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- Dactylifric acid (3-O-caffeoylshikimic acid)
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Glycosides
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- Ferulic acid glucoside
- p-Coumaric acid glucoside
- 1-Sinapoyl-D-glucose
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Tartaric acid esters
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- Caftaric acid
- Cichoric acid (dicaffeoyltartaric acid)
- Coutaric acid
- Fertaric acid
- Grape reaction product (caftaric acid conjugated with glutathione)
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Other esters
with caffeic acid
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- Caffeoylmalic acid
- Ethyl caffeate
- Methyl caffeate
- Caffeic acid phenethyl ester (CAPE)
- Rosmarinic acid (ester with 3,4-dihydroxyphenyllactic acid)
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Caffeoyl phenylethanoid
glycoside (CPG)
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- Echinacoside
- Calceolarioside A, B, C and F
- Chiritoside A, B and C
- Cistanoside A, B, C, D, E, F, G an H
- Conandroside
- Myconoside
- Pauoifloside
- Plantainoside A
- Plantamajoside
- Tubuloside B
- Verbascoside (Isoverbascoside, 2'-Acetylverbascoside)
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| Oligomeric forms |
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Dimers
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- Diferulic acids (DiFA) : 5,5'-Diferulic acid, 8-O-4'-Diferulic acid, 8,5'-Diferulic acid, 8,5'-DiFA (DC), 8,5'-DiFA (BF), 8,8'-Diferulic acid
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Trimers
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- Triferulic acids : 5-5',8'-O-4"-Triferulic acid
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Tetramers
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Conjugates with
coenzyme A (CoA) |
- Caffeoyl-CoA
- Cinnamoyl-CoA
- Coumaroyl-CoA
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UpToDate Contents
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English Journal
- Interaction between natural antioxidants derived from cinnamon and cocoa in binary and complex mixtures.
- Muhammad DRA1, Praseptiangga D2, Van de Walle D3, Dewettinck K4.
- Food chemistry.Food Chem.2017 Sep 15;231:356-364. doi: 10.1016/j.foodchem.2017.03.128. Epub 2017 Mar 23.
- PMID 28450018
- Perceived bitterness character of beer in relation to hop variety and the impact of hop aroma.
- Oladokun O1, James S1, Cowley T1, Dehrmann F1, Smart K1, Hort J1, Cook D2.
- Food chemistry.Food Chem.2017 Sep 1;230:215-224. doi: 10.1016/j.foodchem.2017.03.031. Epub 2017 Mar 8.
- PMID 28407903
- Octadecylimidazolium ionic liquid-modified magnetic materials: Preparation, adsorption evaluation and their excellent application for honey and cinnamon.
- Liu H1, Li Z2, Takafuji M3, Ihara H3, Qiu H4.
- Food chemistry.Food Chem.2017 Aug 15;229:208-214. doi: 10.1016/j.foodchem.2017.02.080. Epub 2017 Feb 20.
- PMID 28372166
Japanese Journal
- Synthesis of Amide and Ester Derivatives of Cinnamic Acid and Its Analogs: Evaluation of Their Free Radical Scavenging and Monoamine Oxidase and Cholinesterase Inhibitory Activities
- Biological activities and antibacterial biomarker of <i>Sesbania grandiflora</i> bark extract
- An improvement of LLNA:DA to assess the skin sensitization potential of chemicals
Related Links
- [trans-Cinnamic Acid] [140-10-3] | 価格や在庫、物性値などの詳細情報ページです。 ... ・川口の在庫は即日，つくばの在庫は2〜3日以内の出荷となります。・詳細につきましては，お手数ですが営業部までお問い合わせください。
- Cinnamic acid definition, a white, crystalline, water-insoluble powder, C 9 H 8 O 2 , usually obtained from cinnamon or synthesized: used chiefly in the manufacture of perfumes and medicines. See more. Thesaurus Translate ...
Related Pictures
★リンクテーブル★
[★]
- 英
- cinnamic acid、cinnamate
- 関
- 桂皮酸塩、ケイ皮酸、桂皮酸エステル
[★]
桂皮酸エステル、桂皮酸塩、桂皮酸
- 関
- cinnamic acid
[★]
- 英
- cinnamic acid
- 関
- 桂皮酸
