Cinnamyl alcohol
Cinnamyl alcohol
CAS: 104-54-1
Molecular Formula: C9H10O
Cinnamyl alcohol - Names and Identifiers
| Name | Cinnamyl alcohol |
| Synonyms | 3-PHENYLALLYLOL Cinnamic alcohol 3-PHENYLPROPENOL Cinnamyl alcohol 3-phenylpropan-1-ol 3-PHENYLALLYL ALCOHOL 3-phenylprop-2-en-1-ol 3-PHENYL-2-PROPEN-1-OL TRANS-CINNAMYL ALCOHOL 3-Phenyl-2-propen-1-ol 3-PHENYL-2-PROPENE-1-OL 3-Phenyl-2-propene-1-ol (E)-3-phenylprop-2-en-1-ol (2Z)-3-phenylprop-2-en-1-ol (2E)-3-phenylprop-2-en-1-ol TRANS-3-PHENYL-2-PROPEN-1-OL 3-HYDROXY-1-PHENYL-1-PROPENE |
| CAS | 104-54-1 |
| EINECS | 203-212-3 |
| InChI | InChI=1/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+ |
| InChIKey | OOCCDEMITAIZTP-QPJJXVBHSA-N |
Cinnamyl alcohol - Physico-chemical Properties
| Molecular Formula | C9H10O |
| Molar Mass | 134.18 |
| Density | 1.044 g/mL at 25 °C (lit.) |
| Melting Point | 30-33 °C (lit.) |
| Boling Point | 250 °C (lit.) |
| Flash Point | >230°F |
| JECFA Number | 647 |
| Water Solubility | 1.8 g/L (20 ºC) |
| Solubility | Soluble in ethanol, propylene glycol and most non-volatile oils, insoluble in water and petroleum ether, insoluble in glycerin and non-volatile oils. |
| Vapor Presure | <0.01 mm Hg ( 25 °C) |
| Vapor Density | 4.6 (vs air) |
| Appearance | White to yellowish crystals or colorless to yellowish liquids |
| Specific Gravity | 1.044 |
| Color | White |
| Merck | 14,2302 |
| BRN | 1903999 |
| pKa | 0.852[at 20 ℃] |
| Storage Condition | -20°C |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Sensitive | Sensitive to light |
| Refractive Index | 1.5819 |
| MDL | MFCD00002921 |
| Physical and Chemical Properties | Density 1.044 melting point 31-35°C boiling point 258°C refractive index 1.5819 flash point 126°C water-soluble 1.8g/L (20°C) |
| Use | Widely used in the preparation of flower flavor, cosmetic flavor and soap flavor, also used as fixative |
Cinnamyl alcohol - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R36/38 - Irritating to eyes and skin. R43 - May cause sensitization by skin contact R36 - Irritating to the eyes |
| 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. S37/39 - Wear suitable gloves and eye/face protection S24 - Avoid contact with skin. S24/25 - Avoid contact with skin and eyes. |
| UN IDs | 2811 |
| WGK Germany | 2 |
| RTECS | GE2200000 |
| FLUKA BRAND F CODES | 10-23 |
| TSCA | Yes |
| HS Code | 29062990 |
| Toxicity | LD50 (g/kg): 2.0 orally in rats; >5.0 dermally in rabbits (Letizia) |
Cinnamyl alcohol - Upstream Downstream Industry
| Downstream Products | flunarizine dihydrochloride |
Cinnamyl alcohol - Reference
| Reference Show more | 1. Liu Yuebo, Zhang Xiaomin, Hong Bing, et al. HPLC-DAD method to compare the content of effective ingredients in different dosage forms of Mahuang Decoction and its prescription [J]. China 2020 of traditional Chinese medicine science and technology (1). 2. Bian Xiaokun, Zhao Qiulong, Bu Fanshu, et al. Effects and evaluation of different drying methods on phenylpropanoids in Guizhi [J]. 2020 of Modern Chinese Medicine v.22(02):71-75. 3. 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]. Northwestern Journal of Pharmacy 2020 35(01):24-29. 4. Liu Chong, Liu Yinzhen, Le Zhiyong, et al. Study on Quality Standard of Guizhi Decoction [J]. Chinese Herbal Medicine, 2017(8). 5. Guo Shuang, Liang Li, Li Qing, et al. Study on Correlation between Cinnamon Microscopic Characteristic Index and Chemical Composition [J]. Shi Zhen Chinese Medicine, 2016, 027(010):2312-2315. 6. Zhang Xinshu, Dong Jinxiang, Yang Jingyao, Zhang Yuhang, Chang Baijin, Gao Han, Xu Wei, Qiu Zhidong, Jia Ailing. Study on Reference Fingerprint and Multi-index Value Transfer of Classical Fangbaoyuan Decoction [J]. Journal of Pharmaceutical Analysis, 2021,41(02):345-358. 7. Zhang Yong, Ding Yue, Zhang Tong, Wang Bing, Wang Xinhong, Wu Weigang. Evaluation of Cinnamon with Different Growth Years by HPLC Fingerprint Combined with Stoichiometric Method [J]. Chinese patent medicine, 2021,43(02):543-546. 8. Zheng, Mengkai, 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." Journal of ethnopharmacology 164 (2015): 22-29.https:// 9. [IF = 4.411] Ninghui Ma et al. "Chemical Fingerprinting and Quantification of Chinese Cinnamomi Cortex by Ultra High Performance Liquid Chromatography Coupled with Chemometrics Methods." Molecules. 2018 Sep;23(9):2214 10. [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 11. [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 12. [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 |
Cinnamyl alcohol - Nature
Open Data Verified Data
is a colorless to yellowish needle-like crystal with an aroma similar to that of hyacinth. Soluble in ethanol and other organic solvents, difficult to dissolve in water. It is gradually oxidized to cinnamaldehyde in long-standing air.
Last Update：2024-01-02 23:10:35
Cinnamyl alcohol - Preparation Method
Open Data Verified Data
The Styrax was saponified by heating in a sodium hydroxide solution, extracted and distilled under reduced pressure. Alternatively, cinnamaldehyde can be prepared by reduction of aluminum isopropenyl, aluminum butanol or aluminum benzyl alcohol.
Last Update：2022-01-01 10:07:34
Cinnamyl alcohol - Use
Open Data Verified Data
used in food flavor and daily flavor formulations. In the edible spices, mainly used for the preparation of strawberry, lemon, apricot, peach and other fruit-based food flavor and flavor of brandy. The amount of chewing gum used was 720mg/kg; 33mg/kg in baked food; 17mg/kg in candy; 8.8mg/kg in soft drinks; 8.7 mg/kg in cold drinks; And 5.0 mg/kg in alcohol.
Last Update：2022-01-01 10:07:34
Cinnamyl alcohol - Reference Information
| Plant source: | Cinnamon |
| FEMA | 2294 | CINNAMYL ALCOHOL |
| LogP | 1.452 at 25℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| traits | cinnamyl alcohol is white to yellowish crystal or colorless to yellowish liquid. |
| properties | cinnamon alcohol is soluble in most non-volatile oils, insoluble in water and petroleum ether, insoluble in glycerin and non-volatile oils. |
| use | cinnamon alcohol natural products exist in peruvian balsam, cinnamon leaves, hyacinth oil and suhe balsam in the form of esters. Commonly used as fixative and modifier. It is also shared with phenylacetaldehyde. It is an indispensable spice for preparing daffodil flavors, rose flavors and other floral flavors. It can also be used to prepare apricot, peach, raspberry, plum and other flavors, cosmetic flavors and soap flavors. It has a mild, lasting and comfortable aroma and elegant fragrance. It is also an important pharmaceutical raw material, often used in the synthesis of cardiovascular and cerebrovascular drugs, such as Naoyizine. It can effectively inhibit the lung tumor caused by the virus; it is clinically used for blood cancer, uterine cancer, ovarian tumor, esophageal cancer and other tumors. Cinnamyl alcohol is an edible spice that is temporarily allowed in the GB2760-96. It is mainly used to prepare strawberry, lemon, apricot, peach and other fruit-type edible flavors and Prynne GB 2760-96 stipulates that it is temporarily allowed to use edible spices. Mainly used for apricot, peach, raspberry, plum and other flavors. It is widely used in the preparation of floral flavor, cosmetic flavor and soap flavor, and also used as fixer cinnamon is a food flavor temporarily allowed to be used in China's "Hygienic Standard for the Use of Food Additives". It is mainly used in the preparation of strawberry, lemon, apricot, peach and other fruit flavor and brandy flavor. The amount used in chewing gum is 720 mg/kg; 33 mg/kg in baked food; 17 mg/kg in candy; 8.8 mg/kg in soft drinks; 8.7 mg/kg in cold drinks; Alcohol 5.0 mg/kg. spices; fixative; preservatives; deodorant. It has a mild, long-lasting and comfortable aroma, elegant fragrance, and has the ability to fix the fragrance. It is used in cosmetics, flavors and soap flavors. It is often shared with phenylacetaldehyde and is an indispensable spice for preparing daffodil and rose flavors. |
| content analysis | determined by total alcohol content determination method (GT-5). The amount of acetylated alcohol used for saponification is 1g, and the equivalent factor (e) in the calculation is 67.0g. Or by non-polar column method in GT-10-4. |
| toxicity | ADI 1.25 mg/kg(CE). LD502000mg/kg (rat, oral). |
| usage limit | FEMA(mg/kg): soft drink 8.8; Cold drink 8.7; Candy 17; Baked food 33; Pudding 22; Gum candy 720; Wine 5.0. Moderate limit (FDA § 172.515,2000). |
| production method | cinnamon alcohol is stored in natural Suhe oil, Peruvian gum and cinnamon oil in the form of ester, and an appropriate amount of 10% caustic solution is added. It can be prepared by heating. There are many ways to synthesize cinnamyl alcohol. Cinnamyl cinnamate is saponified in alkaline medium to obtain cinnamyl alcohol with good quality; cinnamyl aldehyde is reduced by isopropenyl aluminum to obtain cinnamyl alcohol in a 73% yield; when cinnamyl aldehyde is reduced with benzyl alcohol aluminum When cinnamaldehyde, it will be steamed into benzaldehyde at the same time to obtain cinnamyl alcohol. The finished product is distilled under reduced pressure. The cinnamaldehyde is reduced by this method without touching the double bond of the side chain. cinnamaldehyde reduction method adds 0.01 parts of aluminum chips to 1 part of benzyl alcohol, heats to 60 ℃ to react and release hydrogen, and the temperature rises to 180 ℃ until hydrogen release is stopped. The benzyl alcohol aluminum solution is cooled and filtered and added to the mixture of benzyl alcohol and cinnamaldehyde (mass 1:1). Under the condition of 0.0027MPa heating to boiling, at 80 degrees C and reflux ratio of 3~4 steam out of the reaction of benzaldehyde, while adding benzyl alcohol. Until the theoretical amount of 95% benzaldehyde is steamed out, the feeding is stopped, and the remaining benzyl alcohol is steamed out, and then the crude cinnamon alcohol is steamed out. After vacuum distillation, the fraction at 117 ℃(7kPa) is collected, which is the product. Styrax saponification method Cinyl alcohol is naturally present in Peruvian balsam, benzoin and Styrax in the form of cinnamate. Styrax greens are heated and saponified in a 10% sodium hydroxide solution for 5h, and the hydrolysate cinnamyl alcohol is extracted with ether, and finally purified by vacuum distillation to obtain the finished product. The sulac fat containing cinnamate is saponified in the same amount of 10% caustic soda solution for 5 hours to obtain the hydrolysate cinnamol and cinnamic acid, then ether is used to produce cinnamol and purified by vacuum distillation. Soluble cinnamaldehyde in isopropanol, catalyzed by aluminum isopropoxide, fractionated at 70~80 ℃, reduced distillate is crude, then evaporated to isopropanol and reduced pressure distillation, purification, that is, pure product. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:49:11
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