Basic information
- CAS
551-08-6- Standard SMILES
CCCC=C1OC(=O)c2ccccc21- InChIKey
WMBOCUXXNSOQHM-UHFFFAOYSA-N- Molecular formula
- C12H12O2
- Average molar mass
- 188.22 g/mol
- Monoisotopic mass
- 188.08372962
Overview
butylidenephthalide has been reported in Angelica gigas, Apiaceae, and other organisms with data available.
Names & identifiers
- Preferred name
- 1(3H)-Isobenzofuranone, 3-butylidene-
- IUPAC
- 3-butylidene-2-benzofuran-1-one
- English name
- 3-Butylidenephthalide
- Molecular formula
- C12H12O2
- Molecular weight
- 188.22
Names & synonyms
3-butylidene-2-benzofuran-1-one1(3H)-ISOBENZOFURANONE, 3-BUTYLIDENE-DTXSID9060281RefChem:408849DTXCID2041836Butylidene phthalide3-Butylidene phthalide3-butylideneisobenzofuran-1-onecis-Butylidenephthalide;(Z)-ButylidenephthalideSCHEMBL290483orb1222058SCHEMBL11040192
Show more names
3-BUTYLIDENEPHTHALIDEBdphFEMA 3333N-BUTYLIDENEPHTHALIDEligusticumlactone3-butylidene-phthalid3-Butylideneisobenzofuran-1(3H)-oneAi3-37306NSC 325307
SCHEMBL11040195SCHEMBL11041324SCHEMBL29372485WMBOCUXXNSOQHM-UHFFFAOYSA-NXCA91731AKOS028108549DB-315286NS00080374
Database identifiers
- CAS
551-08-6- PubChem CID
- 62368
- DTXSID
DTXSID9060281
Properties
Computed structural properties
- XLogP
- 3.2
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 255
Physicochemical properties
- Melting point
- 82.5 °C · 82.5°C
- Boiling point
- 139 · 139-142 °C/5 mmHg (lit.)
- Density
- 1.103 g/mL · 1.103 g/mL at 25 °C (lit.)
- refractive index
- 20 · n 20/D 1.577 (lit.)
- FLAVIS Number
- 10.024 · 10.024 | 3-Butylidenephthalide
- FEMA
- 3333 · 3333 | 3-BUTYLIDENEPHTHALIDE
- Flash point
- 113 °C · 113 °C - closed cup
- storage temp.
- Refrigerator
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly)
- form
- Oil
- color
- Colourless to Yellow
- Odor
- 10 % · at 10.00 % in dipropylene glycol. herbal lovage celery
- Odor Type
- herbal
- biological source
- synthetic
- JECFA Number
- 1170 · 1170
- BRN
- 5145 · 5145
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory Information
Chemical: 1(3H)-Isobenzofuranone, 3-butylidene-
1(3H)-Isobenzofuranone, 3-butylidene-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 1(3H)-Isobenzofuranone, 3-butylidene-: Environment tier I assessment
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- TI3692500
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 23
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 2
- Precautionary statements
- P264-P270-P301+P312a-P330-P501a
Chemistry & industry
Uses & manufacturing
General Manufacturing Information1(3H)-Isobenzofuranone, 3-butylidene-: ACTIVE
Applications
DescriptionN-Butylidenephthalide is a phthalide derivative useful for control of sensation disorder and olfaction disorder. It is a bioactive phthalide compound of Chuanxiong rhizoma, a Chinese herbal medicine used for treating headache obtained from the root of Ligusticum chuanxiong Hort. It has found that it can regulate tumor stem cell genes EZH2/AXL and reduced its migration and invasion in glioblastoma. Moreover, it can induce apoptosis in the A549 human lung adenocarcinoma cell line by coupled down-regulation of AP-2a and telomerase activity. Therefore, it is a potential cancer chemotherapy drug. Moreover, It can also exhibit protection against neurotoxicity through regulation of tryptophan 2, 3 dioxygenase in spinocerebellar ataxia type 3. Finally, it has certain antiplatelet effect.
OccurrenceReported as occurring naturally in the fruits and roots of Ligusticum acutilobum and lovage (Levisticum officinale) seeds, roots and leaves.
Uses3-Butylidenephthalide is a phthalide derivative useful for control of sensation disorder and olfaction disorder.
General Description3-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.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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