Cas no 81944-09-4 ((Z)-Ligustilide)

(Z)-Ligustilide structure
(Z)-Ligustilide structure
Product Name:(Z)-Ligustilide
CAS No:81944-09-4
MF:C12H14O2
MW:190.238363742828
MDL:MFCD01861511
CID:722356
PubChem ID:5319022
Update Time:2024-10-27

(Z)-Ligustilide Chemical and Physical Properties

Names and Identifiers

    • 1(3H)-Isobenzofuranone, 3-butylidene-4,5-dihydro-, (3Z)-
    • 3-BUTYLIDEN-4,5-DIHYDRO-3H-ISOBENZOFURAN-1-ONE
    • 3-BUTYLIDENE-4,5-DIHYDROPHTHALIDE
    • LIGUSTILIDE, Z-
    • Z-LIGUSTILIDE
    • 3-Butylidene-4,5-dihydro-1(3H)-isobenzofuranone
    • 1(3H)-Isobenzofuranone,3-butylidene-4,5-dihydro-
    • (3Z)-3-Butylidene-4,5-dihydroisobenzofuran-1(3H)-one
    • Ligustilide
    • Ligustilide A
    • LIGUSTILLIDE A
    • (3Z)-3-Butylidene-4,5-dihydro-1(3H)-isobenzofuranone
    • 1(3H)-Isobenzofuranone, 3-butylidene-4,5-dihydro-
    • KBio2_002182
    • Spectrum_001702
    • SpecPlus_000585
    • Spectrum4_001816
    • KBioSS_002182
    • KBioGR_002456
    • DivK1c_006681
    • KBio2_007318
    • KBio2_004750
    • KBio1_001625
    • 3-butylidene-4,5-dihydro-2-benzofuran-1(3h)-one
    • 1(3H)-Isobenzofuranone, 3-butylidene-4,5-dihydro-, (E)-
    • (Z)-Ligustilide
    • (Z)-3-Butylidene-4,5-dihydroisobenzofuran-1(3H)-one
    • (3Z)-3-butylidene-4,5-dihydro-2-benzofuran-1-one
    • cis-ligustilide
    • 10HE68JD06
    • trans-ligustilide
    • Ligusticide
    • Ligustilide, (E)-
    • Spectrum5_000551
    • (3Z)-3-butylidene-4,5-dihydroisobenzofuran-1-one
    • (3Z)-3-Butylidene-4,5-dihydro-1(3H)-isobenzofuranone (ACI)
    • 1(3H)-Isobenzofuranone, 3-butylidene-4,5-dihydro-, (Z)- (ZCI)
    • (1E)-2-(4-Chlorophenyl)-3-(4-morpholinyl)-N-[(Z)-4-pyridinylmethylidene]-3-thioxo-1-propen-1-amine
    • 81944-09-4
    • 3-Butylidene-4,5-dihydro-1(3H)-isobenzofuranone;1(3H)-Isobenzofuranone,3-butylidene-4,5-dihydro-;(3Z)-3-Butylidene-4,5-dihydroisobenzofuran-1(3H)-one
    • MFCD01861511
    • Ligustilide, >=98% (HPLC)
    • SCHEMBL11967666
    • 1ST40092
    • CHEBI:68232
    • BDBM50441016
    • BRD-K48875051-001-01-0
    • DA-64972
    • Q27136725
    • F30153
    • HY-N0401
    • 1(3H)-Isobenzofuranone, 3-butylidene-4,5-dihydro-, (Z)-
    • UNII-10HE68JD06
    • BCP09458
    • CS-5299
    • CHEMBL481246
    • Ligustilide?
    • CCG-266505
    • s9385
    • 4431-01-0
    • AKOS006276856
    • AC-8049
    • Q-100482
    • C16987
    • AS-15334
    • DA-79127
    • MDL： MFCD01861511
    • 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-
    • InChI Key： IQVQXVFMNOFTMU-FLIBITNWSA-N
    • SMILES： C(=C1/OC(=O)C2C=CCCC/1=2)/CCC

Computed Properties

  • Exact Mass: 190.09900
  • Monoisotopic Mass: 190.099379685 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 345
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Molecular Weight: 190.24
  • XLogP3: 2.7
  • Topological Polar Surface Area: 26.3

Experimental Properties

  • Color/Form: A solution in ethanol
  • Density: 1.10±0.1 g/cm3 (20 oC 760 Torr),
  • Solubility: Slightly soluble (1.2 g/l) (25 o C),
  • PSA: 26.30000
  • LogP: 2.87380

(Z)-Ligustilide Security Information

  • Signal Word：Warning
  • Storage Condition：Dry, dark and store at 0-4℃ for short term (days to weeks) or -20℃ for long term (Store correctly 2-3years).

(Z)-Ligustilide Pricemore >>

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(Z)-Ligustilide Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Methanesulfonyl chloride Solvents: Dichloromethane
1.2 Reagents: Pyridine Solvents: Dichloromethane
Reference
Addition of methyl thioglycolate and benzylamine to (Z)-ligustilide, a bioactive unsaturated lactone constituent of several herbal medicines. An improved synthesis of (Z)-ligustilide
Beck, John J.; Stermitz, Frank R., Journal of Natural Products, 1995, 58(7), 1047-55

Production Method 2

Reaction Conditions
1.1 Reagents: Pyridine ,  Methanesulfonyl chloride Solvents: Dichloromethane ;  -10 °C
1.2 Reagents: Pyridine ;  115 °C
Reference
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
Sheng, Bingbing; Vo, Yen; Lan, Ping ; Gardiner, Michael G.; Banwell, Martin G. ; et al, Organic Letters, 2019, 21(16), 6295-6299

Production Method 3

Reaction Conditions
1.1 Catalysts: Silver iodide Solvents: Dimethylformamide
Reference
Efficient synthesis of naturally occurring ligustilide
Ogawa, Yoshimitsu; Maruno, Masao; Wakamatsu, Takeshi, Synlett, 1995, (8), 871-2

Production Method 4

Reaction Conditions
1.1 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Tetrahydrofuran ;  30 min, 150 °C
Reference
Structural Reassignment of rel-(3'Z,3R,6R,7R,3a'R,6'R)-3,8-Dihydrodiligustilide and the Activity of Diligustilide and 3,8-Dihydro- and 3,8,7',7a'-Tetrahydrodiligustilides as Progestins
Avila, Jose Luis; Almeida-Aguirre, Ericka K. P.; Mendez-Cuesta, Carlos A.; Toscano, Ruben A.; Cerbon Cervantes, Marco A.; et al, Organic Letters, 2019, 21(18), 7460-7465

(Z)-Ligustilide Raw materials

(Z)-Ligustilide Preparation Products

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