551-08-6 Usage
Description
N-Butylidenephthalide is a phthalide derivative useful for control of sensation disorder and olfaction disorder. It is a bioactive phthalide compound of Chuanxiong rhizoma, a Chinese herbal medicine used for treating headache obtained from the root of Ligusticum chuanxiong Hort. It has found that it can regulate tumor stem cell genes EZH2/AXL and reduced its migration and invasion in glioblastoma. Moreover, it can induce apoptosis in the A549 human lung adenocarcinoma cell line by coupled down-regulation of AP-2a and telomerase activity. Therefore, it is a potential cancer chemotherapy drug. Moreover, It can also exhibit protection against neurotoxicity through regulation of tryptophan 2, 3 dioxygenase in spinocerebellar ataxia type 3. Finally, it has certain antiplatelet effect.
Reference
Lin, Po Cheng, et al. "Orphan nuclear receptor, Nurr‐77 was a possible target gene of butylidenephthalide chemotherapy on glioblastoma multiform brain tumor." Journal of Neurochemistry 106.3(2010):1017-1026.
Rajamani, K, et al. "n-Butylidenephthalide exhibits protection against neurotoxicity through regulation of tryptophan 2, 3 dioxygenase in spinocerebellar ataxia type 3." Neuropharmacology 117(2017):434-446.
Teng, C. M., et al. "Antiplatelet effect of butylidenephthalide." BBA General Subjects 924.3(1987):375-382.
Chemical Properties
3-Butylidenephthalide has a pervasive warm spicy aroma.
Occurrence
Reported as occurring naturally in the fruits and roots of Ligusticum acutilobum and lovage (Levisticum officinale)
seeds, roots and leaves.
Uses
3-Butylidenephthalide is a phthalide derivative useful for control of sensation disorder and olfaction disorder.
Definition
ChEBI: A gamma-lactone that is phthalide substituted by a butylidene group at position 3. Isolated from Ligusticum porteri, it exhibits hypoglycemic activity.
Taste threshold values
Taste characteristics at 15 ppm: celery, green, vegetable-like with a herbal nuance.
General Description
3-Butylidenephthalide is a bioactive phthalide compound of Chuanxiong rhizoma, a Chinese herbal medicine used for treating headache obtained from the root of Ligusticum chuanxiong Hort.
Safety Profile
Moderately toxic by
ingestion. A skin irritant. When heated to
decomposition it emits acrid smoke and
irritating fumes.
Check Digit Verification of cas no
The CAS Registry Mumber 551-08-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 1 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 551-08:
(5*5)+(4*5)+(3*1)+(2*0)+(1*8)=56
56 % 10 = 6
So 551-08-6 is a valid CAS Registry Number.
InChI:InChI=1/C12H12O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-8H,2-3H2,1H3/b11-8+
551-08-6Relevant articles and documents
Synthetic method of food additive tetrabutylphthalide and application thereof in seasoning (by machine translation)
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Paragraph 0036; 0039, (2020/06/09)
The synthesized product is used as a main effective component of medicinal plant volatile oil such as angelica sinensis, wallichii and the like; therefore, the product can replace a large amount of natural plants or natural plant extracts, so that the cost is greatly reduced by using the Grignard reagent of natural plants or natural plant extracts of the intermediate 3 - 3 - hydroxyl -3 -butyl -1 (3H) and the traditional Grignard reagent. (by machine translation)
A controllable bulk drug product and its preparation method
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Paragraph 0081-0083, (2018/12/13)
The present invention provides a butyl phthalide raw material drug product with the butyl phthalide content not less than 99.0%; the raw material drug is stable in quality, and can ensure the clinical curative effect and drug safety of a butyl phthalide preparation.
Method used for preparing n-butylphathlide via one pot method
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Paragraph 0023, (2017/01/19)
The invention belongs to the technical field of chemical synthesis, and more specifically relates to a method used for preparing n-butylphathlide via one pot method. The method comprises following steps: phthalic anhydride and valeric anhydride are subjected to a first step reaction under catalytic action of anhydrous sodium acetate, and generated n-pentanoic acid is collected via reduced pressure distillation; a sodium hydroxide solution of sodium borohydride is added into a reaction liquid for a second step of reaction; dichloromethane is used for extracting impurities; pH value is adjusted to be smaller than 7 with an acid for a third step of reaction, dichloromethane is used for extracting, and n-butylphathlide is obtained via concentration. The method is high in yield, low in cost, is safe, and is friendly to the environment.
