3-PHENYLPROPENAL
cinnamaldehyde
CAS: 104-55-2;14371-10-9
Molecular Formula: C9H8O
3-PHENYLPROPENAL - 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 |
3-PHENYLPROPENAL - 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 |
3-PHENYLPROPENAL - 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) |
3-PHENYLPROPENAL - Reference
| Reference Show more | 1. Li Chunhua, Li Jia, Jia Dun, Jia Ying, et al. Study on the Pre-extraction Process of an Inclusion Compound Containing Volatile Oil [J]. Chinese Medicine Guide 2018(1):31-33. 2. Chen Jianhua Happy, Bi Xinning, et al. Intestinal Permeability Characteristics of Rats with Different Ratios of Radix Paeoniae Alba and Guizhi and Their Interaction [J]. Chinese Modern Applied Pharmaceutical 2017(11):1507-1511. 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. 5. Wang Shuqi, Xin Xiaodong, Dun Jiaying, et al. Study on Solubilization of Glycyrrhiza uralensis Fisch Based on Oil-Water Distribution Coefficient and Index Component Content [J]. Journal of Traditional Chinese Medicine, 2020(6). 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. 16. Li Zhuangzhuang, Zhang Jing, Zhao Shaozhe, et al. Optimization of Water Extraction Process of Chaihu Guizhi Granules by Combining Fingerprint and Chemometrics [J]. Chinese Patent Medicine, 2018, v.40(08):199-203. 17. Liu Yuebo, Zhang Xiaomin, Hong Bing, et al.. Comparison of active ingredients in different dosage forms of Mahuang Decoction and its prescriptions by HPLC-DAD method [J]. China Science and Technology 2020 of Traditional Chinese Medicine (1). 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. 20. Liang Zhisen, Chen Yuzhen, Zhou Langjun. Rapid and Simultaneous Detection of Seven Spices in Tea by Ultra Performance Liquid Chromatography-Tandem Mass Spectrometry [J]. Food and Machinery, 2020,36(11):51-57. 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. 23. Wang Huxuan, Zhang Shuqing, Liao Chuan, et al. Evaluation of Antimicrobial Activity and Study on Antimicrobial Mechanism of Plant-derived Active Substances on Lutesomycosis [J]. Journal of Shaanxi University of Science and Technology, 2020, 038(001):P.64-70. 24. Wu Xinhua, Li Changyin, Cao Yuan, Qu Hui, han Yang, Fang Zhuyuan. Based on LC/Q-TOF-MS integration network pharmacology to explore the pharmacodynamic material basis and mechanism of Qianyang Yuyin granule in preventing hypertensive renal damage [J]. Chinese Journal of Experimental Prescription, 2021,27(02):116-129. 25. Lan Jile, Ruan Yeping, Qiu Luqi. Multi-index Optimization of Extraction Process of Fengyin Decoction Based on BAS-GA-BP Neural Network and Entropy Weight Method [J]. Chinese journal of traditional Chinese medicine, 2020,45(23):5686-5693. 26. [IF = 3.414] Mengkai Zheng et al."Effects of herbal drugs in Mahuang decoction and their main components on intestinal transport characteristics of Ephedra alkaloids evaluated by a Caco-2 cell monolayer model." J Ethnopharmacol. 2015 Apr;164:22 27. [IF = 9.147] Tingting Feng et al."Food-grade Pickering emulsions and high internal phase Pickering emulsions encapsulating cinnamaldehyde based on pea protein-pectin-EGCG complexes for extrusion 3D printing." Food Hydrocolloid. 2022 Mar;124:107265 28. [IF = 6.429] Zhimin Zhou et al."Sustained-release antibacterial pads based on nonwovens polyethylene terephthalate modified by β-cyclodextrin embedded with cinnamaldehyde for cold fresh pork preservation." Food Packaging Shelf. 2020 Dec;26:100554 29. [IF = 6.429] Yufan Yang et al."Fabrication and characterization of cinnamaldehyde loaded polysaccharide composite nanofiber film as potential antimicrobial packaging material." Food Packaging Shelf. 2020 Dec;26:100600 30. [IF = 5.81] Cui Lihua et al."Chaihu Guizhi Ganjiang Decoction Ameliorates Pancreatic Fibrosis via JNK/mTOR Signaling Pathway." Front Pharmacol. 2021 Jun;0:1369 31. [IF = 4.225] Wei Wenyang et al."Screening of Antiviral Components of Ma Huang Tang and Investigation on the Ephedra Alkaloids Efficacy on Influenza Virus Type A." Front Pharmacol. 2019 Sep;0:961 32. [IF = 3.616] Feng Jia et al."Development and characterization of gliadin-based bioplastic films enforced by cinnamaldehyde." J Cereal Sci. 2021 May;99:103208 33. [IF = 0.986] Ji-le Lan et al."Q-marker Prediction Analysis of Rhubarb in Fengyin Decoction Based on Fingerprint and Network Pharmacology:." Nat Prod Commun. 2021;16(8): 34. [IF = 2.63] Zhou Peng et al."Exploring the Mechanism of Ling-Gui-Zhu-Gan Decoction in Ventricular Remodeling after Acute Myocardial Infarction Based on UPLC and In Vivo Experiments." Evidence-based Complementary and Alternative Medicine. 2022;2022:8593176 |
3-PHENYLPROPENAL - 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
3-PHENYLPROPENAL - 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
3-PHENYLPROPENAL - 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
3-PHENYLPROPENAL - Application
Open Data Verified Data
for the formulation of spices. It can also be used as a food preservative.
Last Update：2025-08-19 16:24:40
3-PHENYLPROPENAL - 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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