3-Butylidenephthalide - ≥96%, mixture of cis and trans isomers , CAS No.551-08-6

CAS: 551-08-6 Cat. No.: B138989 Molecular Weight: 188.22 EC Number: 208-991-3

GRADE & PURITY ≥96%, mixture of cis and trans isomers

Synonyms

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 | BUTYLIDENEPHTHALIDE, (Z)- | NSC325307 | NSC-325307 | (Z)-3-butylideneisobenzofuran-1(3H)-one | 3-Butylideneisobenzofuran-1(3H)-one | WMBOCUXXNSOQHM-FLIBITNWSA-N | AC-34145 | 3

Storage

Room temperature

Shipped In

Normal

Overview

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.

Specifications

Synonyms

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 | BUTYLIDENEPHTHALIDE, (Z)- | NSC325307 | NSC-325307 | (Z)-3-butylideneisobenzofuran-1(3H)-one | 3-Butylideneisobenzofuran-1(3H)-one | WMBOCUXXNSOQHM-FLIBITNWSA-N | AC-34145 | 3

Specifications & Purity

≥96%, mixture of cis and trans isomers

Storage

Room temperature

Shipped In

Normal

Purity

≥96%

Names and Identifiers

• Pubchem Sid: 488190938
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488190938
• Canonical Smiles: CCCC=C1C2=CC=CC=C2C(=O)O1
• IUPAC Name: (3Z)-3-butylidene-2-benzofuran-1-one
• InChIKey: WMBOCUXXNSOQHM-FLIBITNWSA-N
• INCHI: 1S/C12H12O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-8H,2-3H2,1H3/b11-8-
• Isomeric SMILES: CCC/C=C\1/C2=CC=CC=C2C(=O)O1
• WGK Germany: 3
• RTECS: TI3692500
• Molecular Weight: 188.22
• Reaxy-Rn: 5145
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=5145&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Isocoumarans
      • Subclass Isobenzofuranones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Isocoumarans
• Subclass: Isobenzofuranones
• Intermediate Tree Nodes: Not available
• Direct Parent: Isobenzofuranones
• Alternative Parents: Benzenoids Enol esters Lactones Oxacyclic compounds Monocarboxylic acids and derivatives Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Isobenzofuranone - Benzenoid - Enol ester - Lactone - Carboxylic acid ester - Oxacycle - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as isobenzofuranones. These are compounds containing a 2-benzofuran moiety that carries an oxo group at the 1 position.
• External Descriptors: 2-benzofurans - gamma-lactone

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Htr7 Serotonin 7 (5-HT7) receptor (19 Activities)

Discover Target: Htr7

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Drosophila melanogaster (359 Activities)

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Ctenocephalides felis (292 Activities)

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Trpa1 Transient receptor potential cation channel subfamily A member 1 (1003 Activities)

Discover Target: Trpa1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trpm8 Transient receptor potential cation channel subfamily M member 8 (889 Activities)

Discover Target: Trpm8

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Bemisia tabaci (599 Activities)

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Plasma (328 Activities)

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Dermatophagoides farinae (123 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Refractive Index: n20/D 1.577
• Boil Point(°C): 139-142 °C/5 mmHg
• Molecular Weight: 188.220 g/mol
• XLogP3: 3.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 188.084 Da
• Monoisotopic Mass: 188.084 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 255.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Zhijun Wang, Xiaomeng Tang, Lei Lv, Sicong Qiao, Mengxin Chen, Hongjie Song.  (2025)  HPTLC-Bioautography–MS-Guided Strategy for the Detection of Phthalides With Antimicrobial and Antioxidant Activities From Ligusticum chuanxiong Essential Oil.  PHYTOCHEMICAL ANALYSIS,      [PMID:39805321] [10.1002/pca.3498]

2. Wenzhi Li, Jiling Ma, Youhua Long, Weizhen Wang, Xianhui Yin, Zhuzhu Zhang, Bingce Wang, Lu Yang, Hujun Qin.  (2026)  Antifungal mechanisms of volatile organic compounds from Streptomyces albidoflavus SC-3 against postharvest kiwifruit rot caused by Botryosphaeria dothidea.  FOOD MICROBIOLOGY,      [PMID:41722972] [10.1016/j.fm.2026.105053]