3-butyl-1(3h)-isobenzofuranon
3-butylphthalide
CAS: 6066-49-5
Molecular Formula: C12H14O2
3-butyl-1(3h)-isobenzofuranon - Names and Identifiers
| Name | 3-butylphthalide |
| Synonyms | CL234 CCRIS 7107 FEMA No. 3334 Butylphthalide Butylphathlide 3-butylphthalide 3-Butylphthalide 3-n-Butylphthalide Phthalide, 3-butyl- BUTYLPHTHALIDE, 3-n-(P) Butyphthalide impurity 49 3-Butylisobenzofuran-1(3H) 3-butyl-1(3h)-isobenzofuranon 3-Butyl-1(3H)-isobenzofuranone 3-Butylisobenzofuran-1(3H)-one 3-butyl-2-benzofuran-1(3H)-one 1(3H)-Isobenzofuranone, 3-butyl- 6a-(4-chlorophenyl)-8-[(4-fluorophenyl)amino]-6-(4-hydroxy-3-iodo-5-methoxyphenyl)-2-[2-(4-hydroxyphenyl)ethyl]-3a,4,6,6a,9a,10,10a,10b-octahydroisoindolo[5,6-e]isoindole-1,3,7,9(2H,8H)-tetrone |
| CAS | 6066-49-5 |
| EINECS | 228-000-8 |
| InChI | InChI=1/C41H34ClFIN3O7/c1-54-33-19-22(18-32(44)36(33)49)35-28-14-15-29-34(39(52)46(37(29)50)17-16-21-2-12-27(48)13-3-21)30(28)20-31-38(51)47(45-26-10-8-25(43)9-11-26)40(53)41(31,35)23-4-6-24(42)7-5-23/h2-14,18-19,29-31,34-35,45,48-49H,15-17,20H2,1H3 |
3-butyl-1(3h)-isobenzofuranon - Physico-chemical Properties
| Molecular Formula | C12H14O2 |
| Molar Mass | 190.24 |
| Density | 1.0527 (rough estimate) |
| Boling Point | 265.75°C (rough estimate) |
| Specific Rotation(α) | -59.5°( chloroform) |
| Flash Point | 493.5°C |
| JECFA Number | 1169 |
| Solubility | Soluble in methanol, DMSO and other solvents |
| Vapor Presure | 1.01E-33mmHg at 25°C |
| Appearance | Colorless oil |
| Color | Colourless to Yellow |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Stability | Hygroscopic |
| Refractive Index | 1.5197 (estimate) |
| MDL | MFCD01704513 |
| Physical and Chemical Properties | Paste, soluble in methanol, ethanol, DMSO and other organic solvents, derived from Ligusticum as the main component, Ligusticum Chuanxiong, Angelica sinensis Angelica acutiloba(Sieb.et Zucc.) Kitag. Root, celery seed. |
3-butyl-1(3h)-isobenzofuranon - Reference
| Reference Show more | 1. Wang Jingjing, Liang, Juanjuan, Chen, er, M, et al. Evaluation of main phthalide components in Tianshu capsules by one-Test multi-evaluation method combined with UPLC-Q-TOF/MS [J]. Chinese Journal of Experimental prescriptions 2015 021(022):86-93. 2. Zhou Fei, Zhang Jingwen, Wang Wei. Preventive effect and mechanism of butylphthalide on myocardial ischemia reperfusion injury in rats [J]. China pharmacy 2017 28(025):3518-3521. 3. Huang you, Chen, Haiyun, He Chaoming, et al. Effects of butylphthalide on oxidative stress inflammatory pathway in rats with cerebral ischemia-reperfusion injury [J]. Journal of Xi'an Jiaotong University: medical science 2020. 4. Peng Tong, Wang Yinquan, Zhang Yali, Yan Shunan, Qin Jun, Ma Qin state. Comparison of 8 effective components between Angelica sinensis of Linqu and Minxian County [J]. Journal of Gansu University of Chinese Medicine, 2020,37(06):29-33. 5. Zhang, natiing, et al. "Pharmacokinetics-based identification of potential therapeutic overhead from XueBiJing, a Chinese herb injection used in sepsis management." Drug Metabolism and Disposition 46.6 (2018): 823-834.DOI: https://doi.org/10.1124/dmd.11 6. [IF=4.932] Zhiwang Wang et al."Butylphthalide ameliorates airway inflammation and mucus hypersecretion via NF-κB in a murine asthma model."Int Immunopharmacol. 2019 Nov;76:105873 |
3-butyl-1(3h)-isobenzofuranon - Reference Information
| FEMA | 3334 | 3-N-BUTYLPHTHALIDE |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | butylphthalide is divided into n-butylphthalide and butylphthalide, chemical name is 3-butyl -1(3H)-isobenzofuranone, also known as apigenin A, trade name is enbipu, is a simple phthalide, oily liquid, celery flavor, is China's independent research and development for the treatment of ischemic stroke drugs, it has excellent safety of a single body structure, at the same time has a variety of pharmacological effects, can comprehensive treatment of ischemic stroke significantly reduce the loss of neurological function after infarction, improve the living ability of patients. |
| Application | butylphthalide commonly known as celery A, it is the main component of celery volatile oil, it is also widely found in other plants of the Umbelliferae and Compositae family. Apigenin A has strong anticonvulsant, Antiasthmatic, inhibiting prostaglandin F2x hyperplasia, increasing blood flow, A variety of pharmacological activities, such as anti-tumor and anti-hypertension, indicate that it has broad application prospects in clinical practice. In addition, celery a with a natural banana fragrance, can also be used in the food industry. |
| preparation | add 60.0g of phthalic anhydride, 113.2g of valeric anhydride and 33.23g of anhydrous sodium acetate into a 500ml reaction flask, the temperature is raised to 200 ℃ for 3H, the reaction is completed, and the resultant N-pentanoic acid is concentrated and recovered under reduced pressure. The temperature is cooled to 30 ℃, and sodium hydroxide solution of sodium borohydride (6.5g Sodium Borohydride, 40.0g sodium hydroxide dissolved in 100ml water) is slowly added, after reaction at 60 ℃ for 5h, the impurities were extracted with dichloromethane at the end of the reaction, the pH of the aqueous phase was adjusted to 1 with dilute hydrochloric acid, and the temperature was maintained at 85 ℃ for 3H. After cooling, dichloromethane was extracted and concentrated to obtain 54.2g of N-butylphthalide, with a yield of 70.33%, the purity of the liquid phase was 98.36%. |
| Use | n-butylphthalide can resist cerebral ischemia and senile dementia. for content determination/identification/pharmacological experiments. Pharmacological Efficacy: spasmolytic and inhibition of uterine contraction. |
| category | toxic substances |
| toxicity grade | poisoning |
| Acute toxicity | oral-rat LD50: 2450 mg/kg |
| stimulation data | Skin-rabbit 500 mg/24 h moderate |
| flammability hazard characteristics | thermal decomposition of spicy and irritating smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying |
| fire extinguishing agent | water, dry powder, carbon dioxide, foam |
Last Update：2024-04-09 02:00:09
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