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

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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

Visible Light-Promoted Magnesium, Iron, and Nickel Catalysis Enabling C(sp3)-H Lactonization of 2-Alkylbenzoic Acids

A mild and practical C(sp3)-H lactonization protocol has been achieved by merging photocatalysis and magnesium (iron, nickel) catalysis. A diverse range of 2-alkylbenzoic acids with a variety of substitution patterns could be transformed into the corresponding phthalide products. Based on the mechanistic experimentation and reported prior studies, a possible mechanism for the benzylic oxidative lactonization reaction was proposed with the hypothetic photoactive ternary complex formed between the 2-alkylbenzoic acid substrate, magnesium ion, and bromate anion.

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.

α-Angelica lactone catalyzed oxidation of benzylic sp3C-H bonds of isochromans and phthalans

A metal-free organocatalytic system has been developed for highly efficient benzylic C-H oxygenations of cyclic ethers using oxygen as an oxidant. This oxidation reaction utilizes α-angelica lactone as a low cost/low molecular weight catalyst. The optimized reaction conditions allow the synthesis of valued isocoumarins and phthalides from readily available precursors in good yields. Mechanistic studies indicate that the reaction pathway likely involves a radical processviaa peroxide intermediate.