Ligustilide - 10mM in DMSO , CAS No.4431-01-0

CAS: 4431-01-0 Cat. No.: L424013 Formula: C₁₂H₁₄O₂ Molecular Weight: 190.238 EC Number: 809-243-4

GRADE & PURITY 10mM in DMSO

Synonyms

STK500619 | BCP09458 | (3Z)-3-butylidene-4,5-dihydro-2-benzofuran-1-one. | Ligustilide, >=98% (HPLC) | s9385 | (3Z)-3-butylidene-4,5-dihydro-2-benzofuran-1-one | cis-ligustilide | HY-N0401 | 3-Butylidene-4,5-dihydro-1(3H)-isobenzofuranone;1(3H)-Isobenzofu

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Ligustilide is a phthalide derivative that has been shown to have broad applications in the study and treatment of cardiovascular diseases and ischemic brain injury.

Specifications

Synonyms

STK500619 | BCP09458 | (3Z)-3-butylidene-4,5-dihydro-2-benzofuran-1-one. | Ligustilide, >=98% (HPLC) | s9385 | (3Z)-3-butylidene-4,5-dihydro-2-benzofuran-1-one | cis-ligustilide | HY-N0401 | 3-Butylidene-4,5-dihydro-1(3H)-isobenzofuranone;1(3H)-Isobenzofu

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Ligustilide can inhibit the proliferation of and cell cycle progression of vascular smooth muscle cells and inhibits vasoconstriction. It increases vasodilation, anti-thrombosis, and serotonergic activity and decreases platelet aggregation.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Pubchem Sid: 528775579
• Canonical Smiles: CCCC=C1C2=C(C=CCC2)C(=O)O1
• IUPAC Name: (3Z)-3-butylidene-4,5-dihydro-2-benzofuran-1-one
• InChIKey: IQVQXVFMNOFTMU-FLIBITNWSA-N
• INCHI: 1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h5,7-8H,2-4,6H2,1H3/b11-8-
• Isomeric SMILES: CCC/C=C\1/C2=C(C=CCC2)C(=O)O1
• Alternate CAS: 81944-09-4
• Molecular Weight: 190.238
• Reaxy-Rn: 1344345
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1344345&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Isobenzofurans

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Isobenzofurans
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Isobenzofurans
• Alternative Parents: Butenolides Enol esters Enoate esters Lactones Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Isobenzofuran - 2-furanone - Dihydrofuran - Enol ester - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Carboxylic acid ester - Lactone - Carboxylic acid derivative - Oxacycle - Monocarboxylic acid or derivatives - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organooxygen compound - Carbonyl group - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety.
• External Descriptors: butenolide

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(Human)

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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Associated Targets(non-human)

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

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Hdac6 Histone deacetylase 6 (222 Activities)

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MAL62 Alpha-glucosidase MAL62 (106 Activities)

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Drosophila melanogaster (359 Activities)

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Aedes aegypti (630 Activities)

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Mus musculus (284745 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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

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Anopheles stephensi (118 Activities)

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Bemisia tabaci (599 Activities)

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Colletotrichum fragariae (147 Activities)

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Colletotrichum gloeosporioides (560 Activities)

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nAChRbeta2 Acetylcholine receptor subunit beta-like 2 (115 Activities)

Discover Target: nAChRbeta2

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Colletotrichum acutatum (300 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Boil Point(°C): 169℃/mmHg
• Melt Point(°C): 159℃
• Molecular Weight: 190.240 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 190.099 Da
• Monoisotopic Mass: 190.099 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 345.000
• 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. Shasha He, Xuhua He, Shujuan Pan, Wenwen Jiang.  (2023)  Exploring the Mechanism of Chuanxiong Rhizoma against Thrombosis Based on Network Pharmacology, Molecular Docking and Experimental Verification.  MOLECULES,  28  (18): (6702).  [PMID:37764479] [10.3390/molecules28186702]

2. Zhengyong Wang, Yuqi Cao, Yingjie Lu, Fang Zhang, Yue Su, Yinlong Guo.  (2020)  Ultrasonic extraction and nebulization in real-time coupled with carbon fiber ionization mass spectrometry for rapid screening of the synthetic drugs adulterated into herbal products.  ANALYTICA CHIMICA ACTA,      [PMID:33081950] [10.1016/j.aca.2020.08.045]