N-BUTYLIDENEPHTHALIDE Chemical Properties

Melting point:

82.5°C

Boiling point:

139-142 °C/5 mmHg (lit.)

Density 

1.103 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.577(lit.)

FEMA 

3333 | 3-BUTYLIDENEPHTHALIDE

Flash point:

>230 °F

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Oil

color 

Colourless to Yellow

Odor

at 10.00 % in dipropylene glycol. herbal lovage celery

Odor Type

herbal

JECFA Number

1170

BRN 

5145

InChIKey

WMBOCUXXNSOQHM-FLIBITNWSA-N

LogP

3.72

CAS DataBase Reference

551-08-6(CAS DataBase Reference)

EPA Substance Registry System

1(3H)-Isobenzofuranone, 3-butylidene- (551-08-6)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

23

WGK Germany 

2

RTECS 

TI3692500

TSCA 

Yes

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N-BUTYLIDENEPHTHALIDE Usage And Synthesis

Description

N-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.

Reference

• Lin, Po Cheng, et al. "Orphan nuclear receptor, Nurr‐77 was a possible target gene of butylidenephthalide chemotherapy on glioblastoma multiform brain tumor." Journal of Neurochemistry 106.3(2010):1017-1026.
• Rajamani, K, et al. "n-Butylidenephthalide exhibits protection against neurotoxicity through regulation of tryptophan 2, 3 dioxygenase in spinocerebellar ataxia type 3." Neuropharmacology 117(2017):434-446.
• Teng, C. M., et al. "Antiplatelet effect of butylidenephthalide." BBA General Subjects 924.3(1987):375-382.

Chemical Properties

3-Butylidenephthalide has a pervasive warm spicy aroma.

Occurrence

Reported as occurring naturally in the fruits and roots of Ligusticum acutilobum and lovage (Levisticum officinale) seeds, roots and leaves.

Uses

3-Butylidenephthalide is a phthalide derivative useful for control of sensation disorder and olfaction disorder.

Definition

ChEBI: A gamma-lactone that is phthalide substituted by a butylidene group at position 3. Isolated from Ligusticum porteri, it exhibits hypoglycemic activity.

Taste threshold values

Taste characteristics at 15 ppm: celery, green, vegetable-like with a herbal nuance.

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.

Safety Profile

Moderately toxic by ingestion. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

target

Nrf2 | TNF-α | NO | IL Receptor

N-BUTYLIDENEPHTHALIDE(551-08-6)Related Product Information

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