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

Chemical Properties

3-N-Butylphthalide has a warm, spicy herbaceous odor.

Occurrence

Reported found in Levisticum officinale (lovage) and L. acutilobum; also in celery oil.

Uses

3-Butylphthalide is a cardiovascular drug used for the treatment of cerebral ischemic stroke.

Preparation

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

Aroma threshold values

Detection: 5 ppb

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 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 550-37-8 2-pentanoylbenzoic acid 
• 85-44-9 phthalic anhydride 
• 111973-81-0 C₁₂H₁₃IO₂ 
• 136715-61-2 13-Oxa-tricyclo[6.4.1.0^2,7]trideca-2⁽⁷⁾,3,5-trien-1-ol 
• 31274-15-4 7,8-Benzobicyclo[4.2.0]okt-7-en-1-ol 
• 73621-23-5 4,4-Dimethyl-2-(2-vinyl-phenyl)-4,5-dihydro-oxazole 
• 425642-64-4 1-butyl-4-penten-2-ynyl (Z)-5-trimethylsilyl-2-penten-4-ynoate 
• 425642-48-4 1-butyl-4-penten-2-ynyl (Z)-2-penten-4-ynoate 
• 425642-59-7 3-butyl-4-vinylphthalide 
• 162050-42-2 3-hydroxy-3-butyl-1(3H)-isobenzofuranone 

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.

Design, Synthesis and Antifungal Activities of 6-Substituted 3-Butylphthalide Derivatives against Phytopathogenic Fungi

In order to discover novel potential antifungal agents, a series of 6-substituted 3-butylphthalide derivatives were designed, synthesized and evaluated for their antifungal activities against nine phytopathogenic fungi. Preliminary bioassay tests showed that five 3-butylphthalide derivatives exhibited more potent antifungal activities than hymexazol at the concentration of 50 μg/mL. Especially, 3-butyl-6-nitro-2-benzofuran-1(3H)-one and 3-butyl-6-hydroxy-5-nitro-2-benzofuran-1(3H)-one had significant fungicidal activity against some phytopathogenic fungi. The EC50 of 3-butyl-6-nitro-2-benzofuran-1(3H)-one against FS, FO and FG were 6.6, 9.6 and 16.0 μg/mL, respectively. The EC50 of 3-butyl-6-hydroxy-5-nitro-2-benzofuran-1(3H)-one against BC, PO, VM, SS and AS were 6.3, 5.9, 10.0, 4.5 and 8.4 μg/mL, respectively. The preliminary structure–activity relationships (SARs) of all target compounds were also investigated.