CINNAMIC ALDEHYDE

CINNAMIC ALDEHYDE - Names and Identifiers

Name	cinnamaldehyde
Synonyms	FEMA 2286 Zimtaldehyd AKOS B004060 CINNAMALDEHYDE cinnamaldehyde 3-PHENYLPROPENAL AKOS BBS-00003207 CINNAMIC ALDEHYDE Cinnamyl Aldehyde Cinnamic aldehyde 3-Phenyl-2-propenal 3-phenylprop-2-enal 2-phenylprop-2-enal trans-Cinnamaldehyde CINNAMALDEHYDE, TRANS- LABOTEST-BB LT00939010 (2E)-3-phenylprop-2-enal (2Z)-3-phenylprop-2-enal NATURAL CINNAMYL ALDEHYDE trans-3-Phenyl-2-propenal
CAS	104-55-2 14371-10-9
EINECS	203-213-9
InChI	InChI=1/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4-
InChIKey	KJPRLNWUNMBNBZ-QPJJXVBHSA-N

CINNAMIC ALDEHYDE - Physico-chemical Properties

Molecular Formula	C9H8O
Molar Mass	132.16
Density	1.05 g/mL at 25 °C (lit.)
Melting Point	−9-−4°C(lit.)
Boling Point	248 °C (lit.)
Flash Point	160°F
JECFA Number	656
Water Solubility	Slightly soluble
Solubility	Insoluble in petroleum ether, slightly soluble in water, soluble in volatile or non-volatile grease, and miscible with ethanol, ether and chloroform.
Vapor Density	4.6 (vs air)
Appearance	Colorless or light yellow liquid
Specific Gravity	1.05
Color	Clear yellow
Odor	Strong odor of cinnamon
Merck	13,2319
pKa	0[at 20 ℃]
Storage Condition	Store below +30°C.
Stability	Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
Sensitive	Sensitive to light
Refractive Index	n20/D 1.622(lit.)
MDL	MFCD00007000
Physical and Chemical Properties	Density 1.05 melting point -7.5°C boiling point 251°C refractive index 1.61 flash point 71°C water-soluble soda solution
Use	Spices used as solvents, food flavoring agents and chemicals

CINNAMIC ALDEHYDE - Risk and Safety

Hazard Symbols	Xi - Irritant
Risk Codes	R36/37/38 - Irritating to eyes, respiratory system and skin. R43 - May cause sensitization by skin contact
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves.
UN IDs	UN8027
WGK Germany	3
RTECS	GD6476000
FLUKA BRAND F CODES	10-23
HS Code	29122900
Toxicity	LD50 in rats (mg/kg): 2220 orally (Jenner)

CINNAMIC ALDEHYDE - Reference

Reference

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3. Zhang Qianxia, Chen Shaoli, Wen Xiaopan, and other important medicine of Wuling Powder "Guizhi" in the renal protection of Wuling Powder on adriamycin nephropathy rats [J]. Journal of Traditional Chinese Medicine 2019 60(02):65-69.
4. Dunjiaying, Zheng Peng, Li Jiajia, et al. Response Surface Methodology Combined with Information Entropy Theory to Optimize the Extraction Process of Taohe Chengqi Soup [J]. Chinese Pharmacy 2019 v.30; no.658 (16):55-60.
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6. Liu Linqi, Zhao Chenxi, Li Jingfeng, et al. Microwave extraction process and antioxidant effect of cinnamon active ingredients [J]. Modern Food Science and Technology, 2017, 033(011):127-133.
7. Gao Yan, Zheng Mengcheng, Du Shouying, et al. Study on preparation process of cinnamaldehyde liposome [J]. Journal of Tianjin University of Traditional Chinese Medicine, 2019, 38(02):180-185.
8. Li Dan, Zhao Yue, Li Tingting, etc. Effects of Oil Varieties on Formation and Properties of Cinnamic Acid-based Oil Gel [J]. Food Science, 2018, 39(012):9-14.
9. Ding Yutong, Zhao Ruizhi, Wang Yang. Effects of sheep oil roasted epimedium on dissolution of main active ingredients in Chishao Powder [J]. Shi Zhen Guo Yi Guo Yao, 2020, v.31;No.293(01):63-65.
10. Zeng Qiongyao, Zhang Wenjing, Zhang Yu, et al. Effect of cinnamon oil active ingredient (E)-cinnamaldehyde on proliferation and apoptosis of colon cancer cells [J]. Chinese Clinical Pharmacology and Therapeutics, 2019(9).
11. Li Xinling, Kang Huaibin, zhang Huiyun. Preparation and Characterization of Cinnamon Essential Oil Nanocapsules and Their Antibacterial and Antioxidant Capacity in Vitro [J]. Food and Fermentation Industry, 2019, v.45;No.395(23):125-131.
12. Wang Yuqiong, Han Rui, Liu Dandan, et al. Determination of Toxicity of Cinnamaldehyde to Pig Small Intestinal Epithelial Cells [J]. Heilongjiang Animal Husbandry and Veterinary Medicine, 2014, 000(005):166-168.
13. Zheng Peng, li Jiajia, Dun Jiaying, et al. Study on the Stability of Volatile Oil in Tingli Shengmai Oral Liquid [J]. Shi Zhen Guo Yi Guo Yao, 2018, 29(11):102-104.
14. Mi Jia, He Wenda, Liang Xinyi, et al. Cluster Analysis of Fingerprint and Quantitative Analysis of Multiple Indexes of Coptis Cinnamomi Drugs [J]. Shi Zhen Guo Yi Guo Yao, 2019, 30(01):83-86.
15. Wang Shuyu, Wang Ziyuan, Zhang Min. Inhibitory effects of different bacteriostats on Bacillus cereus in fresh wet surface of highland barley [J]. Food Science, 2020,41(13):206-211.
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18. Zhang Qi Jiayu, Sun Yi, Chen Hao, Zhao Chongbo, Zuo Zhenyu, Xue Lei, Wu Jianhua. Optimization of Microwave Processing Process of Cinnamon Branches by Response Surface Methodology [J]. Northwest Journal of Pharmacy 2020 35(01):24-29.
19. Guo Shuang, Liang Li, Li Qing, et al. Study on Correlation between Microscopic Characteristic Index of Cinnamon and Chemical Composition [J]. Shi Zhen Guo Yi Guo Yao, 2016, 027(010):2312-2315.
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21. Chen Xugang, Qu Shulan, Chen Long. LC-MS-based study on the effect of cinnamaldehyde on metabonomics in mice with acute ulcerative colitis [J]. Pharmacology and Clinic of Traditional Chinese Medicine, 2021,37(01):88-96.
22. Zhao Qiulong, Bian Xiaokun, Qian Dawei, Su Shulan, Guo Sheng, Wang Tuanjie, Duan Jinguo. Metabolites of Guizhi Fuling Capsule in Plasma, Bile, Urine and Feces of Primary Dysmenorrhea Model Rats [J]. Journal of Pharmaceutical Analysis, 2021,41(01):51-63.
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CINNAMIC ALDEHYDE - Nature

Open Data Verified Data

is a colorless to pale yellow oily liquid. It has a strong cinnamon aroma with sweet and hot aroma. It is easily oxidized by air, and the oxidation product is cinnamic acid. Molecular weight 132. 17, boiling point 246 ℃, melting point -7.5 ℃, flash point 120 ℃, relative density of 1. 049~1. 055, refractive index of 1.619~1.625. Soluble in ethanol, ether, chloroform, insoluble in water and glycerol.

Last Update：2024-01-02 23:10:35

CINNAMIC ALDEHYDE - Preparation Method

Open Data Verified Data

cinnamaldehyde exists in a variety of essential oils, with the highest content of cinnamon oil in China, up to 85% ~ 90%. Cinnamaldehyde is separated from cinnamon oil. The traditional chemical separation method is to use sodium bisulfite and aldehyde group nucleophilic addition to form salt crystal precipitation (but this reaction can also produce stable 1,4 addition disulfonate compound, with water-soluble easy to waste), and then NaOH decomposition will be more pure cinnamaldehyde; Such as acetic anhydride reaction made Diethyl ester, and then crystallization filtration, and then dilute sulfuric acid decomposition can also be more pure cinnamaldehyde; the fractionation method can also obtain relatively pure cinnamaldehyde.

Last Update：2022-01-01 11:14:26

CINNAMIC ALDEHYDE - Introduction

The product is unstable in nature and easy to oxidize to cinnamic acid. It will be tested as soon as possible within one week after receiving the goods.

Last Update：2022-10-16 17:11:40

CINNAMIC ALDEHYDE - Use

Open Data Verified Data

for the formulation of spices. It can also be used as a food preservative.

Last Update：2022-01-01 11:14:27

CINNAMIC ALDEHYDE - Reference Information

Plant source:	Cinnamon
FEMA	2286 \| CINNAMALDEHYDE
LogP	1.83-2.1 at 25-27℃
NIST chemical information	Information provided by: webbook.nist.gov (external link)
EPA chemical information	Information provided by: ofmpub.epa.gov (external link)
use	cinnamaldehyde is one of the important pharmaceutical raw materials. Commonly used in external drugs and synthetic drugs. Because it can promote blood circulation, warm the skin, tighten the skin tissue, and be used for external massage to make the limbs and body comfortable, the phenomenon of water retention can be fully improved, and it has a strong lipolysis effect. It is effective for the softening and removal of skin scars and fibroids. Scattered congestion. It has antithrombin effect, sedative, analgesic, antipyretic, anticonvulsant and other effects. It also has the effect of inhibiting mold. In addition, cinnamaldehyde is one of the important spices, often used in soap flavors, to make mast, vegetarian, lily of the valley, rose and other flavors. Used in food for fruit preservation, etc. The latest research shows that cinnamaldehyde used in chewing gum can have dual effects of sterilization and deodorization. as a preservative, it can be used for the preservation of fruits according to the regulations of our country, and it can be used in an appropriate amount according to the production requirements. It can also be used as a edible spice. China's regulations can be used for the preservation of fruits, and it can be used appropriately according to production needs. It can also be used as a edible spice. Spices; preservatives. GB 2760-96 stipulates that edible spices are allowed to be used. Mainly used to prepare cinnamon, cinnamon, cola flavors, and also used in alcohol and tobacco. The regulations can also be used for fruit preservation, with the dosage GMP; Residual amount ≤ 0.3 mg/kg. Flavoring agent for preparing soap essence, pastry and other foods Solvent, seasoning, pharmaceutical raw material intermediates, essence and spice, etc.
content analysis	method I was determined by non-polar column in GT-10-4 gas chromatography. Method 2 was determined by aldehyde determination method (OT-6), in which the sample amount was 1.5g. The equivalent factor (e) in the calculation is 66.08.
toxicity	ADI has not yet been specified (FAO/WHO,1994)LD50 2220 mg/kg (rat, oral). MNL 125mg/kg (rats). GRAS(FDA § 182.60,2000).
use limit	FEMA(mg/kg): soft drink 9.0; Cold drink. Candy 700; Baked food 180; Gum sugar 4900; Seasoning 20; Meat 60.
production method	cinnamon oil or cinnamon oil is added by sodium bisulfite method, and the adduct of cinnamaldehyde and sodium bisulfite is separated by centrifugation method, washed with ether, decomposed with dilute alkali or acid solution, distilled with water and distilled under reduced pressure. In the presence of sodium hydroxide, it is obtained by condensation of benzaldehyde and acetaldehyde: mix benzaldehyde, acetaldehyde, water and sodium hydroxide solution and oscillate at room temperature for one week, and the obtained oil is extracted with ether, Benzyl dryness, vacuum distillation. Aldol condensation method uses benzaldehyde and acetaldehyde as raw materials to form cinnamaldehyde under alkaline conditions. 133kg of benzaldehyde, 400kg of water, 10kg 40% ~ 50% of sodium hydroxide, 66.6kg of acetaldehyde and 40~50kg of benzene were added to the reaction pot successively, and stirred at 20 ℃ for 5 hours. After the reaction, let it stand and delaminate, take the benzene layer, and then wash it with dilute acid and water until neutral. After benzene is recovered by vacuum distillation, the fraction at 130 ℃(2.67kPa) is collected to obtain 55~60kg of cinnamaldehyde. Essential oil mono-separation method cinnamon oil and Ceylon oil contain about 55% ~ 85% cinnamaldehyde, which can be separated by sodium bisulfite addition method. The adduct is separated by centrifugation, dilute acid or dilute alkali decomposition, steam distillation and vacuum distillation to obtain cinnamaldehyde. (1) hydroxyl condensation method. Benzaldehyde and acetaldehyde are used as raw materials. Condensation under alkaline conditions to produce cinnamaldehyde. 133kg of benzaldehyde, 400kg of water, 10kg 40%-50% of sodium hydroxide, 66.6kg of acetaldehyde and 40-50kg of benzene were added to the reaction pot successively, and stirred at 20 ℃ for 5 hours. After the reaction, let it stand and delaminate, take the benzene layer, and then wash it with dilute acid and water until neutral. After benzene is recovered by vacuum distillation, the fraction at 130 ℃(2.67Kpa) is collected to obtain 55-60kg of cinnamaldehyde. (2) Essential oil separation method. Cinnamon oil and Ceylon oil contain about 55%-85% cinnamaldehyde, which can be separated by sodium bisulfite addition. The adduct is separated by centrifugation, dilute acid or dilute alkali decomposition, steam distillation and vacuum distillation to obtain cinnamaldehyde.
category	toxic substances
toxicity classification	poisoning
acute toxicity	oral administration-rat LD50 2220 mg/kg; Oral administration-mouse LD50: 2225 mg/kg
stimulation data	skin-person 40 mg/48 hours severe
flammability hazard characteristics	combustible, spicy and irritating smoke from the fire site
storage and transportation characteristics	warehouse is low temperature, ventilated and dry; Fire prevention; Store separately from oxidant and food raw materials
fire extinguishing agent	water, carbon dioxide, dry powder, foam
toxic substance data	information provided by: pubchem.ncbi.nlm.nih.gov (external link)

Last Update：2024-04-09 20:48:19

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