6066-49-5

Basic information

• Product Name: 3-N-BUTYLPHTHALIDE
• Synonyms: 3-butyl-1(3h)-isobenzofuranon;3-butyl-1(3H)-Isobenzofuranone;3-butyl-phthalid;3-Butylphthalide;butylphthalide;3-N-BUTYLPHTHALIDE;FEMA 3334;1(3H)-Isobenzofuranone, 3-butyl-
• CAS NO: 6066-49-5
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.24
• EINECS: 228-000-8
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 6066-49-5.mol
• Article Data: 56

Chemical Properties

• Boiling Point: 265.75°C (rough estimate)
• Flash Point: 128.282 °C
• Appearance: /
• Density: 1.0527 (rough estimate)
• Vapor Pressure: 1.01E-33mmHg at 25°C
• Refractive Index: 1.5197 (estimate)
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: 3-N-BUTYLPHTHALIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-N-BUTYLPHTHALIDE(6066-49-5)
• EPA Substance Registry System: 3-N-BUTYLPHTHALIDE(6066-49-5)

Safety Data

• Hazardous Substances Data: 6066-49-5(Hazardous Substances Data)

Usage

Description

3-n-Butylphthalide, also known as 3-Butylphthalide, is an organic compound with a warm, spicy herbaceous odor. It is characterized by its aroma threshold values, with a detection level of 5 ppb. 3-n-Butylphthalide has been found in various plant sources, including Levisticum officinale (lovage) and L. acutilobum, as well as in celery oil. Due to its unique properties, 3-n-Butylphthalide has been identified for its potential applications in the pharmaceutical and food industries.

Uses

Used in Pharmaceutical Industry:
3-n-Butylphthalide is used as a cardiovascular drug for the treatment of cerebral ischemic stroke. Its application in this field is attributed to its ability to improve blood flow and reduce the risk of stroke-related complications.
Used in Flavor and Fragrance Industry:
Given its warm, spicy herbaceous odor, 3-n-Butylphthalide is used as a flavoring agent and fragrance component in the food and beverage industry. Its distinct aroma makes it a valuable addition to various products, enhancing their sensory appeal and consumer experience.

Preparation

From celery oil; from phthalide via bromination and subsequent reaction of the resulting phthalidic acid with n-butyl magnesium bromide.

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

Upstream product

• 109-65-9 1-bromo-butane 
• 16859-59-9 3-hydroxy-1(3H)-isobenzofuranone 
• 693-03-8 n-butyl magnesium bromide 
• 550-37-8 2-pentanoylbenzoic acid 
• 64-19-7 acetic acid 
• 162050-42-2 3-hydroxy-3-butyl-1(3H)-isobenzofuranone 
• 111943-60-3 3-(4-iodobutyl)isobenzofuran-1(3H)-one 
• 1889-20-9 n-butylmagnesium iodide 
• 119-67-5 o-carboxybenzaldehyde 
• 551-08-6 3-butylidenephthalide 
• 380905-48-6 (±)-2-(1-hydroxypentyl)benzoic acid 
• 26311-42-2 2-n-pentylbenzoic acid 
• 693-04-9 butyl magnesium bromide 
• 180068-03-5 n-butyl phthalan 

Downstream Products

• 380905-53-3 (R)-2-(1-hydroxy-n-pentyl)benzoic acid 
• 1330531-02-6 (+/-)-(E)-2-(2-chloroacetoxypentyl)benzoic acid {2-methoxy-4-[2-(3-nitrooxypropoxycarbonyl)vinyl]}phenyl ester 
• 1330531-03-7 (±)-(E)-2-methoxy-4-(3-(4-(nitrooxy)butoxy)-3-oxoprop-1-en-1-yl)phenyl 2-(1-(2-chloroacetoxy)pentyl)benzoate 
• 1330531-04-8 (+/-)-(E)-2-(2-chloroacetoxypentyl)benzoic acid {2-methoxy-4-[2-(5-nitrooxypentoxycarbonyl)vinyl]}phenyl ester 
• 1330531-05-9 (+/-)-(E)-2-(2-chloroacetoxypentyl)benzoic acid {4-[2-(3-nitrooxypropoxycarbonyl)vinyl]}phenyl ester 
• 1330531-06-0 (+/-)-(E)-2-(2-chloroacetoxypentyl)benzoic acid {4-[2-(4-nitrooxybutoxycarbonyl)vinyl]}phenyl ester 
• 1330531-07-1 (+/-)-(E)-2-(2-chloroacetoxypentyl)benzoic acid {4-[2-(5-nitrooxypentoxycarbonyl)vinyl]}phenyl ester 
• 1330531-08-2 (+/-)-(E)-2-[2-(morpholinoacetoxy)pentyl]benzoic acid {2-methoxy-4-[2-(3-nitrooxypropoxycarbonyl)vinyl]}phenyl ester hydrochloride 
• 1330531-09-3 (+/-)-(E)-2-[2-(morpholinoacetoxy)pentyl]benzoic acid {2-methoxy-4-[2-(4-nitrooxybutoxycarbonyl)vinyl]}phenyl ester hydrochloride 
• 1330531-10-6 (+/-)-(E)-2-[2-(morpholinoacetoxy)pentyl]benzoic acid {2-methoxy-4-[2-(5-nitrooxypentoxycarbonyl)vinyl]}phenyl ester hydrochloride 
• 1330531-11-7 (+/-)-(E)-2-[2-(diethylaminoacetoxy)pentyl]benzoic acid {2-methoxy-4-[2-(3-nitrooxypropoxycarbonyl)vinyl]}phenyl ester hydrochloride 
• 1330531-12-8 (+/-)-(E)-2-[2-(diethylaminoacetoxy)pentyl]benzoic acid {2-methoxy-4-[2-(4-nitrooxybutoxycarbonyl)vinyl]}phenyl ester hydrochloride 
• 1330531-13-9 (+/-)-(E)-2-[2-(diethylaminoacetoxy)pentyl]benzoic acid {2-methoxy-4-[2-(5-nitrooxypentoxycarbonyl)vinyl]}phenyl ester hydrochloride 
• 1330531-14-0 (+/-)-(E)-2-[2-(morpholinoacetoxy)pentyl]benzoic acid {4-[2-(3-nitrooxypropoxycarbonyl)vinyl]}phenyl ester hydrochloride 

Relevant articles and documents

Butylphthalide ring-opening compound, pharmaceutical compound, and preparation methods, compositions and applications of butylphthalide ring-opening compound and pharmaceutical compound

The invention relates to the field of medicines, and in particular, relates to a butylphthalide ring-opening compound, a pharmaceutical compound and preparation methods and applications of the butylphthalide ring-opening compound and the pharmaceutical compound. The butylphthalide ring-opening compound has a structure represented by a formula (I), wherein R1 and R2 are the same or different and are independently selected from H, C1-C5 alkyl, C1-C5 hetero-alkyl and -SO2R6, and R6 is selected from H, C1-C5 alkyl, C1-C5 hetero-alkyl, an aromatic ring and a heterocyclic ring from a three-membered ring to an eight-membered ring; or R1 and R2 are connected to form a three-membered ring to an eight-membered ring; and X is C or N or is absent to form a five-membered ring or a six-membered ring. The compound can be fully absorbed by the human body by being combined with an active substance, and the biological activity of the active substance is further promoted. Particularly, after the compound is combined with edaravone, a compound with excellent biological activity can be obtained.

Novel purification method of butylphthalide

The invention aims to provide a simple and easy-to-operate method for preparing high-purity butylphthalide. The method comprises the following steps: subjecting o-formylbenzoic acid to reacting with a Grignard reagent to prepare a reaction solution of butylphthalide, regulating the reaction solution to a certain pH value by using a specific acid at a certain temperature, extracting a product by using an organic solvent, and washing an organic phase by using an alkali so as to obtain high-purity butylphthalide. According to the method, silica gel column chromatography or a high-temperature and high-vacuum distillation method is not used; tedious multiple acid and alkali adjusting procedures for purifying butylphthalide is avoided; operation is simple and effective; and the method is suitable for industrial large-scale production.

Preparation method of high-purity butylphthalide

The invention relates to a preparation method of high-purity butylphthalide. The preparation method comprises the following steps: (1) preparing n-butyl magnesium bromide; (2) synthesizing 2-valerylbenzoic acid; (3) synthesizing butylphthalide; and (4) refining the butylphthalide. Due to the adoption of the technical scheme, the preparation method has the advantages that the n-butyl magnesium bromide is used as an initiator in the step (1), so that the initiation condition is mild, and the safety performance is improved; and the initiation temperature is 38-42 DEG C, and the reaction temperature is only 48-52 DEG C, so that the temperature is easy to implement in the mass production process; the 2-valerylbenzoic acid is used as the raw material, and carbonyl is reduced in a sodium borohydride aqueous solution mode, so that explosion easily caused by a solid feeding mode is avoided, and production safety is guaranteed; and the butylphthalide is refined in a reduced pressure distillationmode, so that the method is simple and easy to implement, and the purity of the obtained high-purity butylphthalide reaches 100%. The synthesis process of butylphthalide is stable, the preparation process is mild and controllable, and the method is suitable for batch production.