Chemical Properties Physical and Chemical Properties Role and purpose Uses Preparation Content Analysis Toxicity Limited use Production method
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Cinnamic acid

Chemical Properties Physical and Chemical Properties Role and purpose Uses Preparation Content Analysis Toxicity Limited use Production method
Product Name
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
Formula Weight
148.16
MOL File
621-82-9.mol
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Cinnamic acid Property

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)
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Usbiological
Product number
300082
Product name
Cinnamic acid
Packaging
20mg
Price
$255
Updated
2021/12/16
TRC
Product number
C442030
Product name
Cinnamic acid
Packaging
100g
Price
$580
Updated
2021/12/16
Chem-Impex
Product number
33956
Product name
Cinnamicacid,99-100%(GC),Natural,meetsFGspecifications,Kosher,FEMA2
Purity
99-100%(GC)
Packaging
1KG
Price
$590.55
Updated
2021/12/16
Chem-Impex
Product number
33956
Product name
Cinnamicacid,99-100%(GC),Natural,meetsFGspecifications,Kosher,FEMA2
Purity
99-100%(GC)
Packaging
2.5KG
Price
$1027.35
Updated
2021/12/16
Chem-Impex
Product number
33955
Product name
Cinnamicacid,99-100%(GC),meetsFGspecifications,KOSHER,FEMA2288
Purity
99-100%(GC)
Packaging
25KG
Price
$1174.12
Updated
2021/12/16
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Cinnamic acid Chemical Properties,Usage,Production

Chemical Properties

Cinnamic acid exists in cis and trans forms. the more stable isomer is the trans isomer, which occurs naturally and is the usual commercial product. It appears as white monoclinic prisms with slight cinnamon aroma. It is soluble in ethanol, methanol, petroleum ether and chloroform; it is easily soluble in benzene, ether, acetone, acetic acid, carbon disulfide and oils but insoluble in water.

Cinnamic acid was first isolated as crystals from cinnamon oil by Trommsdorf in 1780. He thought it was benzoic acid. Dumas and Peligot ´ identified it in 1835, and in 1856 Bertagnini succeeded in synthesizing it from benzaldehyde and acetyl chloride.
Cinnamic acid undergoes reactions typical of a carboxyl group and an olefinic double bond. The carboxyl group can be esterified to form cinnamates, some of which are important flavorings and fragrances. When reacted with inorganic acid chlorides, such as thionyl chloride or phosphorus chlorides, cinnamic acid gives cinnamoyl chloride [102-92-1]. When heated, cinnamic acid forms styrene [100-42-5] and carbon dioxide. With oxidizing agents or when heated with alkali, the olefinic double bond cleaves to give benzaldehyde [98-87-3].

Physical and Chemical Properties

Cinnamic acid, also known benzal acetate, 3-phenyl-2-propenoic acid, belongs to a kind of unsaturated aromatic acid with a slight smell of cinnamon. It is presented in balsam, cinnamon oil and coca leaf in the form of free or ester form. Owing to the presence of a double bond, cinnamic acid has trans-/ cis-two isomers with the cis form containing an extra three kinds of homogeneous polycrystalline. Both trans-form and cis-form are in the presence of nature. The trans-form exists in the presence of essential oils including storax, cinnamon oil, Peruvian balsam, basil oil and cocoa leaves. The cis-form exists in Malacca galangal oil with the trans-form being more stable than the cis-form. The commercially available products are mostly in the form of trans. It has a relative molecular mass of 148.17. The first crystalline form of the cis form is called allocinnamic acid with the compound precipitated from water being monoclinic. It is colorless to white prismatic crystals with the relative density being 1.284 (4 ℃), the melting point being 42 ℃, the boiling point 265 ℃ (decomposition ) and 125 ℃ (2.533 × 103Pa); it is slightly soluble in water (25 ℃ when 0.937) but easily soluble in alcohol, ether and ethyl acetate. The second polymorph is called alpha-iso-cinnamic acid with the compound precipitated from ligroin being the monoclinic crystal. It is colorless to white prismatic crystals with the mp being 58 ℃ and the boiling point being 265 ℃. It is soluble in ethanol, acetic acid, chloroform and acetone and easily soluble in ether. The third polymorph is called beta-iso-cinnamic acid; it appears as monoclinic colorless to white prismatic crystals with the mp being 68 ℃. It is soluble in alcohol, ether, acetic acid, chloroform and acetone. Trans-isomer precipitated from dilute ethanol belongs to the monoclinic crystal and appears as white to pale yellow prismatic crystals with the relative density being 1.2475 (4 ℃), melting point being 133 ℃ and the boiling point being 300 ℃. It is very slightly soluble in water (25 ℃: 0.1; 98 ℃: 0.588), soluble in ethanol (25 ℃: 23), chloroform (15 ℃: 5.9), easily soluble in benzene, ether, acetone, acetic acid and carbon disulfide. When being distilled at 140 ℃, it undergoes decarboxylation to become styrene (Styrax BP). Upon oxidation, it generates benzoic acid. Both the cis-and trans-isomers have flower honey aroma with sweet and spicy flavor. Rat-Oral LD50: 2500 mg/kg.

Role and purpose

Cinnamic acid is an important kind of organic synthetic raw material. It is mainly used for the synthesis of methyl cinnamate, ethyl cinnamate and cinnamic acid benzyl ester. It is widely used in the perfume industry and the pharmaceutical industry. In medicine, it has been ever used as an insect repellent.
Cinnamic acid was used as spices for the preparation of cherry, apricot, honey and cinnamon aromas and flavors; it can also be used as the starting material of cinnamic acid ester. The GB2760-1996 of our country provided that cinnamic acid is allowable edible spices; in addition, it can also be used as the raw material of photosensitive resin poly vinyl cinnamic acid series; it can also be used as the raw material for the synthesis of methyl, ethyl and benzyl esters. These esters, being used as fragrances, can be applied to cosmetics and soap, it can also be used as a local anesthetic, hemostatic agents and pharmaceuticals (lactic acid Prenylamine and baclofen, etc.) raw materials; cinnamic acid may also be used as plant growth regulators and raw materials of pesticides; anti-corrosion agents of fruit and vegetables; raw material of ultraviolet agent and photosensitive resin for cosmetic sunscreen. Cinnamic acid may also be used as the standard for organic trace analysis and determination of double bond, determination of uranium and vanadium and thorium separation.

Uses

Cinnamic acid is an important intermediate in the preparation of its esters, which are used as fragrances, for pharmaceuticals, and for the enzymatic production of l-phenylalanine, the starting material for peptide sweeteners. Sodium cinnamate is a known corrosion inhibitor. Cinnamic acid is also used as a brightener in cyanide-free zinc electroplating baths, a corrosion inhibitor during removal of scale from zinc and in aerosol cans, a low-toxicity heat stabilizer for poly(vinyl chloride) , a cross-linking agent for dimethyl terephthalate – ethylene glycol copolymer and polyurethanes, a fireproofing agent for polycaprolactam, in laundry-resistant polyurethane adhesives for polyester fibers, and for improvement of the storage stability of drying-oil-modified alkyd resin coatings.

Preparation

Cinnamic acid is also produced by Knoevenagel condensation of benzaldehyde with malonic acid in the presence of weakly basic catalysts, such as ammonia and amines.
Reflux together 10ml of benzaldehyde with 10gm of malonic acid and 40ml of 8% ethanolic ammonia solution placed in a 100ml round bottom flask fitted with a reflux condensor on water bath till a clear solution is obtained (about 8-10hours). Set the assembly for downward distillation and distill off the excess alcohol. Continue heating the residual oily portion until the evolution of carbon dioxide ceases. Dissolve the residue in 20ml water, cool and add dilute hydrochloric acid till acidic. Collect the precipitated unsaturated acid on buchner funnel,wash with cold water. Recrystallise from hot water and collect crystals of cinnamic acid, m.p 132°C.

Synthesis of cinnamic acid from benzaldehyde

Content Analysis

Accurately weigh 500 mg of sample which have been previously dried for 3 hours in drier filled with silica gel; add 0.1mol/L hydrogen.

Toxicity

GRAS (FEMA).
The acute oral LD50 in rats is 2.5 g/kg, and the acute dermal LD50 in rabbits exceeds 5 g/kg. Cinnamic acid applied neat to intact or abraded rabbit skin for 24 h was slightly irritating;a4% solution in petrolatum produced no sensitization in man.

Limited use

FEMA (mg/kg): Soft drinks 31; Cold drink 40; Confectionery 30; Bakery 36; Gum 10.
Take moderate as the limit (FDA§172.515, 2000).

Production method

Commercial synthesis of cinnamic acid almost always results in the trans isomer.
The Perkin reaction is the oldest known method of producing cinnamic acid commercially. In this reaction benzaldehyde [100-52-7] is condensed with acetic anhydride in the presence of sodium acetate as catalyst.
Benzal chloride reacts with alkali acetate in an alkaline medium to give a high yield of cinnamic acid. Cinnamic acid can be obtained by this reaction in the presence of amines such as pyridine in more than 80 % yield.
It can also be prepared through: mixing the benzoylacetone, sodium carbonate and bleach, generating sodium cinnamic acid, followed by processing with sulfate.

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

fragrance & flavoring agent, antidiabetic

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.

Uses

Cinnamic Acid is a flavoring agent that consists of crystalline scales, white in color, with an odor resembling honey and flowers. it is slightly soluble in water, soluble in alcohol, chloroform, acetic acid, acetone, benzene, and most oils, and alkali salts soluble in water. it is obtained by chemical synthesis. it is also termed 3-phenylpro- penoic acid.

Definition

ChEBI: A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.

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.

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 1068, 1953 DOI: 10.1021/ja01101a016
The Journal of Organic Chemistry, 59, p. 710, 1994 DOI: 10.1021/jo00083a006

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.

Synthesis

Rainer Ludwig Claisen (1851–1930), German chemist, described for the first time in 1890 the synthesis of cinnamates by reacting aromatic aldehydes with esters. The reaction is known as the Claisen condensation.

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.]

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Cinnamic acid Suppliers

Wuhan lenmaike Industrial Co., Ltd.
Tel
027-83916065 18108665271
Fax
027-83916065
Email
landmarkorganic@qq.com
Country
China
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58
Shandong Fengtai Biotechnology Co., Ltd.
Tel
0531-0531-82066716 15662658391
Fax
0531-82066716
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528732991@qq.com
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China
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1022
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Guangdong Hengtian Biotechnology Co., Ltd.
Tel
15603008518
Fax
15603008518
Email
292064964@qq.com
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China
ProdList
737
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58
Hubei chengfeng chemical co. LTD
Tel
15827338311
Email
1802085297@qq.com
Country
China
ProdList
4005
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58
Zhuhai Anzhe Biotechnology Co,Ltd.
Tel
13570603050
Email
244176264@qq.com
Country
China
ProdList
3015
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58
Huangshi Jingsheng Biotechnology Co., Ltd.
Tel
17771199833; 17771199833
Email
351013952@qq.com
Country
China
ProdList
4607
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58
Zaoyang Cixiang Pharmaceutical Technology Co., LTD
Tel
15671321689
Email
carrie@cixiangyy.com
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China
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19
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58
Beijing Ouhe Technology Co., Ltd
Tel
010-82967028 13552068683
Fax
+86-10-82967029
Email
2355560935@qq.com
Country
China
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12426
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JinYan Chemicals(ShangHai) Co.,Ltd.
Tel
13817811078
Fax
86-021-50426522,50426273
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sales@jingyan-chemical.com
Country
China
ProdList
9984
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Shanghai Longsheng chemical Co.,Ltd.
Tel
021-58099652-8005 13585536065
Fax
021-58099609
Email
bin.wu@shlschem.com
Country
China
ProdList
9816
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View Lastest Price from Cinnamic acid manufacturers

Hebei Yanxi Chemical Co., Ltd.
Product
Cinnamic acid 621-82-9
Price
US $50.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
100000
Release date
2023-09-13
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Cinnamic acid 621-82-9
Price
US $0.00/Kg/Drum
Min. Order
25KG
Purity
99%min
Supply Ability
80tons/month
Release date
2021-06-03
Anhui Yiao New Material Technology Co., Ltd
Product
trans-Cinnamic acid 621-82-9
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1 tons
Release date
2023-11-02

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