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621-82-9

621-82-9 Structure

621-82-9 Structure
IdentificationMore
[Name]

Cinnamic acid
[CAS]

621-82-9
[Synonyms]

2-PROPENOIC ACID, 3-PHENYL-, (2E)-
3-PHENYL-2-PROPENOIC ACID
3-PHENYLACRYLIC ACID
3-PHENYLPROPENOIC ACID
3-STYRYLACRYLIC ACID
AKOS 233-01
AKOS B004228
BETA-PHENYLACRYLIC ACID
CINNAMIC ACID
CINNAMIC ACID, TRANS-
FEMA 2288
RARECHEM BK HC T302
TRANS-3-BENZENEPROPENOIC ACID
TRANS-3-PHENYLACRYLIC ACID
TRANS-3-PHENYLPROPENOIC ACID
TRANS-CINNAMIC ACID
TRANS-CINNAMYLIC ACID
(2E)-3-Phenyl-2-propenoic acid
.beta.-Phenylpropenoicacid
3-Phenyl-2-propenoic acid (cinnamic acid)
[EINECS(EC#)]

205-398-1
[Molecular Formula]

C9H8O2
[MDL Number]

MFCD00004369
[Molecular Weight]

148.16
[MOL File]

621-82-9.mol
Chemical PropertiesBack Directory
[Appearance]

monoclinic crystals
[mp ]

133 °C(lit.)
[bp ]

300 °C(lit.)
[density ]

1.2475
[FEMA ]

2288
[Fp ]

>230 °F
[Stability:]

Stable. Combustible. Incompatible with strong oxidizing agents.
[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.
[CAS DataBase Reference]

621-82-9(CAS DataBase Reference)
[NIST Chemistry Reference]

2-Propenoic acid, 3-phenyl-(621-82-9)
[EPA Substance Registry System]

621-82-9(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[WGK Germany ]

1
[RTECS ]

GD7850000
[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.
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Benzyl chloride-->Sodium acetate trihydrate-->Potassium Acetate-->Calcium hypochlorite-->trans-Cinnamic acid-->Benzalacetone
[Preparation Products]

L-Phenylalanine-->2-[3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-methylphenol-->L-PHENYLALANINE
Questions And AnswerBack Directory
[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.
[Trans-cinnamic acid preparation method]

1. it is extracted from the natural storax.
2. take benzaldehyde as raw material, in the presence of sodium acetate and pyridine; have it have Perkin aldol condensation reaction with acetic anhydride at 190~195 ℃; This will generate the crude product. After the recovery of acetic acid at atmospheric pressure, decolorize with charcoal, and then go through vacuum distillation, cooling and crystallization, recrystallization from ethanol, to obtain purified trans-cinnamic acid. In the above condensation reaction, the α-carbon from the acid anhydride can form bonds with the carbon in the carbonyl group of benzaldehyde, generating β-hydroxy acid anhydride. This intermediate product then further go through two steps including dehydration of acid anhydride and hydrolysis to derive this product.
3. Take dichlorotoluene as starting material; it is heated together with sodium acetate to 190 ℃ in the pyridine solution to give the crude product. After the recovery of acetic acid, go through refinement by recrystallization and then we can get the product of trans-cinnamic acid.
4. Take benzaldehyde and ethyl acetate as raw materials; have them be subject to condensation reaction (Claisen reaction) in the presence of sodium acetate to produce ethyl cinnamate, followed by hydrolysis to obtain the product.
5. Take benzaldehyde and acetone as raw materials; they are heated and subject to condensation reaction in alkaline medium to generate benzylidene acetone, and then use hypochlorite or sodium hypochlorite to oxidize the benzylideneacetone and can generate the crude product of cinnamic acid. After recycling the byproduct chloroform, further go through crystallization, washing and recrystallization to generate the final product.
6. Take benzaldehyde and acetyl chloride as raw materials, perform heating reaction to obtain the crude product. Go through concentration, salting, washing and recrystallization to obtain the refining product.
The above information is edited by the chemicalbook of Xiongfeng Dai.
[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).
LD50 2500 mg/kg (rat, oral)
[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).
[Chemical Properties]

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.
[Uses]

1. It can be used as raw materials for the manufacturing of ester, spices and pharmaceuticals.
2. It can be used for chemical reagents as well as being used for the synthetic of perfume and pharmaceutical.
3. GB 2760-96 provides it for allowable edible flavors. It is mainly used for the preparation of spices and cherries, apricots, honey flavor. It can also applied to the anti-corrosion protection of fresh fruits and vegetables.
[Production method]

1. It can be obtained through the co-heating reaction between benzyl chloride and sodium acetate.
2. It can also be generated through the co-heating reaction between benzaldehyde and sodium acetate (or potassium acetate) in the presence of a dehydrogenating agent.
3. It can also be prepared through: mixing the benzoylacetone, sodium carbonate and bleach, generating sodium cinnamic acid, followed by processing with sulfate.
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