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W333301

Sigma-Aldrich

3-Butylidenephthalide

mixture of cis and trans isomers, ≥96%, FG

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About This Item

Empirical Formula (Hill Notation):
C12H12O2
CAS Number:
551-08-6
Molecular Weight:
188.22
FEMA Number:
3333
EC Number:
208-991-3
Council of Europe no.:
10083
MDL number:
MFCD00047319
UNSPSC Code:
12164502
PubChem Substance ID:
24901649
Flavis number:
10.024
NACRES:
NA.21

biological source

synthetic

grade

FG
Halal
Kosher

reg. compliance

EU Regulation 1334/2008 & 872/2012
FDA 21 CFR 110

Assay

≥96%

refractive index

n20/D 1.577 (lit.)

bp

139-142 °C/5 mmHg (lit.)

density

1.103 g/mL at 25 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

Organoleptic

herbaceous

SMILES string

CCC\C=C1/OC(=O)c2ccccc12

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-

InChI key

WMBOCUXXNSOQHM-FLIBITNWSA-N

General description

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.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H411

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Chyou-wei Wei et al.
Acta pharmacologica Sinica, 30(9), 1297-1306 (2009-08-25)
To investigate the role of hTERT gene expression and AP-2alpha in n-butylidenephthalide (n-BP)-induced apoptosis in A549 lung cancer cells. Viability of A549 cells was measured by MTT assay. Protein expression was determined by Western blot. Telomerase activity was measured using
Sheng-Chun Chiu et al.
PloS one, 7(3), e33742-e33742 (2012-04-04)
N-butylidenephthalide (BP) exhibits antitumor effect in a variety of cancer cell lines. The objective of this study was to obtain additional insights into the mechanisms involved in BP induced cell death in human prostate cancer cells. Two human prostate cancer
Po-Cheng Lin et al.
Journal of neurochemistry, 106(3), 1017-1026 (2008-04-19)
The natural compound n-butylidenephthalide (BP), which is isolated from the chloroform extract of Angelica sinensis, has been investigated for its antitumoral effects on glioblastoma multiform (GBM) brain tumors both in vitro and in vivo. To determine the mechanism of BP-induced
Andreas Schinkovitz et al.
Journal of natural products, 71(9), 1604-1611 (2008-09-11)
Monomeric phthalides such as Z-ligustilide (1) and Z-butylidenephthalide (2) are major constituents of medicinal plants of the Apiaceae family. While 1 has been associated with a variety of observed biological effects, it is also known for its instability and rapid
Yung-Luen Yu et al.
Journal of agricultural and food chemistry, 58(3), 1630-1638 (2010-01-02)
Epigenetic alteration of DNA methylation plays an important role in the regulation of gene expression associated with chemosensitivity of human hepatocellular (HCC) carcinoma cells. With the aim of improving the chemotherapeutic efficacy for HCC, the effect of the naturally occurring
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