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3-Butylidenephthalide

$178

  • Brand : BIOFRON

  • Catalogue Number : BF-B1001

  • Specification : 98%

  • CAS number : 551-08-6

  • Formula : C12H12O2

  • Molecular Weight : 188.22

  • PUBCHEM ID : 642376

  • Volume : 20mg

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Catalogue Number

BF-B1001

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

188.22

Appearance

Colorless paste

Botanical Source

roots of Ligusticum chuanxiong hort

Structure Type

Others

Category

Standards;Natural Pytochemical;API

SMILES

CCCC=C1C2=CC=CC=C2C(=O)O1

Synonyms

1(3H)-Isobenzofuranone, 3-butylidene-, (3Z)-/1(3H)-Isobenzofuranone, 3-butylidene-/3-butylidene-3H-isobenzofuran-1-one/Bdph/N-BUTYLIDENEPHTHALIDE/ligusticumlactone/3-Butylidenephtalide/3-butylidene-phthalid/(3Z)-3-Butylidene-2-benzofuran-1(3H)-one/3-Butylidene Phthalide/BUTYLIDENE PHTHALIDE

IUPAC Name

(3Z)-3-butylidene-2-benzofuran-1-one

Density

1.2±0.1 g/cm3

Solubility

Chloroform; Ethyl Acetate

Flash Point

127.9±23.4 °C

Boiling Point

312.0±35.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:551-08-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31413242

Abstract

The essential oil extracted from roots and rhizomes of Ligusticum jeholense Nakai et Kitagawa was investigated for its chemical composition by GC-MS analysis, and evaluated for its contact toxicity and repellency against Tribolium castaneum and Lasioderma serricorne, along with some of its individual components. The essential oil was rich in aromatics (65.34%) with low molecular weight. Major components included sedanolide (33.95%), 3-butylidenephthalide (18.76%), spathulenol (8.90%) and myristicin (6.76%). The results of bioassays indicated that the essential oil of L. jeholense and 3-butylidenephthalide possessed significant repellent activities against T. castaneum at 2 and 4 h post-exposure. Meanwhile, 3-butylidenephthalide had potent contact toxicity against L. serricorne (LD50 = 13.64 µg/adult). The minor component n-butylbenzene in the oil was highly toxic to T. castaneum (LD50 = 23.99 µg/adult) and L. serricorne (LD50 = 7.86 µg/adult) in contact assays, but failed to repel these beetles at all testing concentrations. Spathulenol and myristicin exerted good insecticidal and repellent effects on the two target insects. This work suggests that the essential oil of L. jeholense has promising potential for development as natural insecticide or repellent to control pest damage in warehouses.

KEYWORDS

Lasioderma serricorne; Ligusticum jeholense; Tribolium castaneum; contact toxicity; essential oil composition; repellency

Title

Bioactivities of 3-Butylidenephthalide and n-Butylbenzene from the Essential Oil ofLigusticum jeholense against Stored-product Insects.

Author

Luo C1, Li DL1, Wang Y2, Guo SS2, Du SS2.

Publish date

2019 Sep 4

PMID

31190814

Abstract

Introduction: Kolliphor® EL (K-EL) is among the most useful surfactants in the preparation of emulsions. However, it is associated with low hydrophobic drug loading in the resulting emulsified formulation. Methods: In this study, a formulation for intranasal administration of butylidenephthalide (Bdph), a candidate drug against glioblastoma (GBM), was prepared. Physical characteristics of the formulation such as particle size, zeta potential, conductivity, and viscosity were assessed, as well as its cytotoxicity and permeability, in order to optimize the formulation and improve its drug loading capacity. Results: The optimized formulation involved the integration of polyethylene glycol 400 (PEG 400) in K-EL to encapsulate Bdph dissolved in dimethyl sulfoxide (DMSO), and it exhibited higher drug loading capacity and drug solubility in water than the old formulation, which did not contain PEG 400. Incorporation of PEG 400 as a co-surfactant increased Bdph loading capacity to up to 50% (v/v), even in formulations using Kolliphor® HS 15 (K-HS15) as a surfactant, which is less compatible with Bdph than K-EL. The optimized Bdph formulation presented 5- and 2.5-fold higher permeability and cytotoxicity, respectively, in human GBM than stock Bdph. This could be attributed to the high drug loading capacity and the high polarity index due to DMSO, which increases the compatibility between the drug and the cell. Rats bearing a brain glioma treated with 160 mg/kg intranasal emulsified Bdph had a mean survival of 37 days, which is the same survival time achieved by treatment with 320 mg/kg stock Bdph. This implies that the optimized emulsified formulation required only half the Bdph dose to achieve an efficacy similar to that of stock Bdph in the treatment of animals with malignant brain tumor.

KEYWORDS

butylidenephthalide; glioblastoma; intranasal administration; loading capacity; permeability; polyethylene glycol 400

Title

Integration of PEG 400 into a self-nanoemulsifying drug delivery system improves drug loading capacity and nasal mucosa permeability and prolongs the survival of rats with malignant brain tumors.

Author

Chen YS1,2,3, Chiu YH3, Li YS3, Lin EY3,4, Hsieh DK5, Lee CH3, Huang MH1, Chuang HM1, Lin SZ1,6, Harn HJ1,7, Chiou TW3.

Publish date

2019 May 16

PMID

31155999

Abstract

Context: Butylidenephthalide (Bdph) has been reported to inhibit rat uterine contractions, but significantly potentiate the noradrenaline (NA)-induced contractions in guinea-pig vas deferens (GPVDs). Objective: The present study elucidates the binding specificity of Bdph in GPVD to potentiate contractions. Materials and methods: Electrical field stimulation (EFS, supramaximal voltage, 1 ms and 1 Hz) or exogenous NA (50 μM) was applied to the GPVD in Krebs or 1/10 Mg-Tyrode’s solution, respectively. After the clonidine (10 nM)-induced twitch inhibition or the exogenous NA-induced contractions reached a constant, Bdph (50 µM) was added 2 min prior to the subsequent addition of NA (50 µM). Three experiments were performed. In the presence of Bdph (100 μM), the release of NA in the medium and remaining NA content in the tissues were determined after EFS-stimulation. Results: Bdph (100 μM) significantly antagonized the clonidine (10 nM)-induced twitch inhibition from 22.5 ± 2.1 to -11.4 ± 1.6% (n = 6) and dibutyryl-cAMP (300 μM) from 25.7 ± 3.2 to 7.9 ± 4.0% (n = 8). Bdph (100 μM) significantly increased the electrically stimulated release of NA from 393.0 ± 109.5 to 1000.0 ± 219.1 ng/g (n = 6). Bdph (50 μM) potentiated the exogenous NA (50 μM)-induced contractions from 3.0 ± 0.06 to 3.9 ± 0.06 g (n = 3), but after washout of Bdph, the response to NA gradually curtailed. Discussion and conclusions: Bdph action may be through the nonspecific binding of the butylidene group to prejunctional α2- and postjunctional α1-adrenoceptors to reversibly block K+ channels, and irreversibly block VDCCs on the smooth muscle cell membrane, respectively.

KEYWORDS

Ca channel blockers; clonidine; noradrenaline; postjunctional K channel blockade; voltage-dependent Ca channels

Title

Butylidenephthalide facilitates contractions via nonspecific binding to receptors in isolated guinea-pig vas deferens.

Author

Shih CH1,2, Chen CM3, Ko WC4.

Publish date

2019 De


Description :

3-Butylidenephthalide (Butylidenephthalide) is a phthalic anhydride derivative identified in Ligusticum chuanxiong Hort, and has larvicidal activity (LC50 of 1.56 mg/g for Spodoptera litura larvae)[1].