72917-31-8

Basic information

• Product Name: (Z)-Butylidenephthalide
• Synonyms: (Z)-Butylidenephthalide;cis-Butylidenephthalide;(3Z)-3-butylidene-2-benzofuran-1-one
• CAS NO: 72917-31-8
• Molecular Formula: C₁₂H₁₂O₂
• Molecular Weight: 188.22248
• Mol File: 72917-31-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 200℃ (1.5 Torr)
• Flash Point: 135.7°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 0.000191mmHg at 25°C
• Refractive Index: 1.567
• CAS DataBase Reference: (Z)-Butylidenephthalide(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-Butylidenephthalide(72917-31-8)
• EPA Substance Registry System: (Z)-Butylidenephthalide(72917-31-8)

Safety Data

• Hazardous Substances Data: 72917-31-8(Hazardous Substances Data)

Usage

Description

(Z)-Butylidenephthalide is an organic compound belonging to the class of phthalides, which are bicyclic organic compounds. It is a colorless to white, crystalline solid with a distinctive odor and is found in certain plants, such as celery, contributing to their characteristic aroma.

Uses

Used in Pharmaceutical Industry:
(Z)-Butylidenephthalide is used as a potential medicinal compound for its anti-inflammatory, anti-cancer, and neuroprotective effects. Its diverse range of biological activities makes it a promising candidate for various therapeutic applications.
Used in Nutraceutical Industry:
(Z)-Butylidenephthalide is used as a natural antioxidant for its ability to protect cells from oxidative damage, which may contribute to overall health and well-being.
Used in Functional Foods:
(Z)-Butylidenephthalide is used as an ingredient in functional foods for its potential to lower blood pressure and cholesterol levels, promoting cardiovascular health.
Used in Aromatherapy:
(Z)-Butylidenephthalide is used as a natural aroma compound in aromatherapy for its distinctive odor, which may have potential benefits for relaxation and mood enhancement.

InChI:InChI=1/C12H14O2/c1-3-11(2)10-12(11)7-5-4-6-8(12)9(13)14-10/h4-8,10H,3H2,1-2H3

Upstream product

• 81944-09-4 Z-ligustilide 
• 85-44-9 phthalic anhydride 
• 2082-59-9 pentanoic anhydride 
• 109-72-8 n-butyllithium 
• 61260-15-9 dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate 
• 123-72-8 butyraldehyde 

Downstream Products

• 380905-48-6 (±)-2-(1-hydroxypentyl)benzoic acid 
• 3413-15-8 butylphthalide 
• 550-37-8 2-pentanoylbenzoic acid 
• 94530-83-3 senkyunolide E 

Relevant articles and documents

A convenient approach for synthesis of (Z)-3-butylidenephthalide derivatives

The reaction of n-BuLi with phthalic anhydride derivatives leads to (Z)-3-butylidenephthalide derivatives.

Direct and Metal-Catalyzed Photochemical Dimerization of the Phthalide (Z)-Ligustilide Leading to Both [2 + 2] and [4 + 2] Cycloadducts: Application to Total Syntheses of Tokinolides A-C and Riligustilide

Synthetically derived (Z)-ligustilide (1) has been subjected to photochemically-promoted dimerization processes under a range of conditions. By such means, varying distributions of the dimeric natural products tokinolides A-C (4, 3, and 6, respectively) and riligustilide (5) as well certain related (isomeric) compounds have been obtained. The structures of three of them have been confirmed by single-crystal X-ray analysis. The biosynthetic implications of the outcomes of this study are discussed.

Preparation method for high-purity butyphthalide

The invention provides a preparation method for high-purity butyphthalide. The method comprises the following steps: S1) taking Raney nickel as a catalyst, performing hydrogenation reaction on butylidene phthalide in an alcohol solvent, removing the solvent at reduced pressure, thereby obtaining a first intermediate; S2) mixing the first intermediate with potassium hydroxide, tetrahydrofuran and water and reacting, and cooling and crystallizing after ending the reaction, thereby obtaining a second intermediate; and S3) performing cyclization reaction on the second intermediate in an acidic organic solvent, thereby obtaining butyphthalide. Compared with the prior art, the preparation method has the advantages that the alcohol solvent and tetrahydrofuran are taken as reaction solvents, can be effectively recycled and are low in cost, so that the production cost is greatly lowered; and meanwhile, the requirement for a refining tower of the production equipment is reduced through the hydrolysis refining, no repeated refining is required, and the energy is saved.