Cinnamic acid
- CAS No.
- 621-82-9
- Chemical Name:
- Cinnamic acid
- Synonyms
- cinnamic;Phenylacrylic acid;3-PHENYLACRYLIC ACID;CINNAMIC ACID, TRANS-;3-PHENYLPROPENOIC ACID;Zimtsaeure;FEMA 2288;AKOS B004228;Cinnamyl Acid;Cinnamic acid(only trans)
- CBNumber:
- CB0345387
- Molecular Formula:
- C9H8O2
- Molecular Weight:
- 148.16
- MOL File:
- 621-82-9.mol
- Modify Date:
- 2024/7/24 13:33:21
| Melting point | 133 °C(lit.) |
|---|---|
| Boiling point | 300 °C(lit.) |
| Density | 1.2475 |
| refractive index | 1.5049 (estimate) |
| FEMA | 2288 | CINNAMIC ACID |
| Flash point | >230 °F |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | Chloroform (Slightly), Methanol (Slightly) |
| form | Solid |
| pka | pK (25°) 4.46 |
| color | White to Off-White |
| PH | 3.76(1 mM solution);3.23(10 mM solution);2.72(100 mM solution) |
| Odor | at 100.00 %. balsam sweet storax |
| Odor Type | balsamic |
| Water Solubility | 511.2mg/L(25 ºC) |
| JECFA Number | 657 |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| LogP | 2.13 |
| CAS DataBase Reference | 621-82-9(CAS DataBase Reference) |
| NIST Chemistry Reference | 2-Propenoic acid, 3-phenyl-(621-82-9) |
| EPA Substance Registry System | Cinnamic acid (621-82-9) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H302-H315-H319-H335 |
| Precautionary statements | P261-P305+P351+P338 |
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 1 |
| RTECS | GD7850000 |
| Toxicity | LD50 (g/kg): 3.57 orally in rats; >5.0 dermally in rabbits (Letizia) |
Cinnamic acid Chemical Properties,Uses,Production
Description
Cinnamic acid is a white crystalline organic acid, which is slightly soluble in water.
It is obtained from oil of cinnamon, or from balsams such as storax. It is also found in shea butter and is the best indication of its environmental history and post-extraction conditions. It can also be made synthetically.
Cinnamic acid is used in flavors, synthetic indigo, and certain pharmaceuticals, though its primary use is in the manufacturing of the methyl, ethyl, and benzyl esters for the perfume industry. Cinnamic acid has a honey- like odor; 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 phenyl propanoid pathways. Its biosynthesis is performed by action of the enzyme phenylalanine ammonia - lyase (PAL) on phenylalanine.
Cinnamic acid is freely soluble in benzene, diethyl ether, acetone, and it is insoluble in hexane.
Cinnamic acid is also a kind of self-inhibitor produced by fungal spore to prevent germination.
Chemical Properties
Cinnamic acid is almost odorless with a burning taste, and then turning sweet and reminiscent of apricot.
Occurrence
The trans- form has been found among the constituents of the essential oils of basil, Chinese cinnamon, Melaleuca bracteata, Alpinia galanga. It is reported found in Peru balsam, Asian and American storax and cocoa leaves. Also reported found in strawberry fruit, beer, cognac, starfruit (Averrhoa carambola L) and loquat. The cis- form is present in the oil of Alpinia malacensis.
Uses
cinnamic acid has sunscreen capabilities. Some manufacturers use it to replace PABA because of its lower allergic and phototoxic reaction incidence. Cinnamic acid is found in cinnamon leaves and cocoa leaves, and is an essential oil of certain mushrooms. It may cause allergic skin rashes.
Preparation
Two isomers, trans- and cis- exist; the trans-isomer is of interest for use in flavoring; in addition to the extraction from natural sources (storax), it can be prepared as follows: (1) from benzaldehyde, anhydrous sodium acetate and acetic anhydride in the presence of pyridine (Perkin reaction); (2) from benzaldehyde and ethyl acetate (Claisen condensation); (3) from benzaldehyde and acetylene chloride; (4) by oxidation of benzylidene acetone with sodium hypochlorite.
Definition
ChEBI: A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.
Safety Profile
Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. A skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and fumes.
Purification Methods
Crystallise the acid from *benzene, CCl4, hot water, water/EtOH (3:1), or 20% aqueous EtOH. Dry it at 60o in vacuo. It is steam volatile. [Beilstein 9 IV 2002.]
Cinnamic acid Preparation Products And Raw materials
Raw materials
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chevron_right| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| Jayshree Aromatics Pvt.Ltd. | +91-9925031256 +91-9925031256 | Gujarat, India | 89 | 58 | Inquiry |
| PERFECT CHEMICAL | +91-9820465461 +91-9820465461 | Mumbai, India | 391 | 58 | Inquiry |
| Shiv Enterprise | +91-9822612471 +91-9822612471 | Maharashtra, India | 10 | 58 | Inquiry |
| Indenta Chemicals (India) Pvt Ltd | +91-2226849600 +91-9326627752 | Maharashtra, India | 48 | 58 | Inquiry |
| Ambe Phytoextracts Private Limited | +91-1143764376 +91-1143764376 | New Delhi, India | 37 | 58 | Inquiry |
| Alfa Aesar | 1 800 209 7001 | Maharashtra, India | 6913 | 58 | Inquiry |
| Triveni chemicals | 08048762458 | New Delhi, India | 6093 | 58 | Inquiry |
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
| Pharma Affiliates | 172-5066494 | Haryana, India | 6761 | 58 | Inquiry |
| ALPHA CHEMIKA | +91-22-22061123 +91-22-66382501 | Mumbai, India | 1681 | 43 | Inquiry |
| Supplier | Advantage |
|---|---|
| Jayshree Aromatics Pvt.Ltd. | 58 |
| PERFECT CHEMICAL | 58 |
| Shiv Enterprise | 58 |
| Indenta Chemicals (India) Pvt Ltd | 58 |
| Ambe Phytoextracts Private Limited | 58 |
| Alfa Aesar | 58 |
| Triveni chemicals | 58 |
| Pharmaffiliates Analytics and Synthetics P. Ltd | 58 |
| Pharma Affiliates | 58 |
| ALPHA CHEMIKA | 43 |
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