3-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

3-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.

Cytotoxicity

The anti-proliferative effects of 3-Butylidenephthalide (n-Butylidenephthalide; BP) on cells from GBM, neuroblastoma, lung cancer, melanoma, teratoma, leukemia, breast cancer and hepatocellular carcinoma, as well as from normal fibroblast and vascular endothelial cells, were determined. The IC50 values of BP after a 48 h incubation with tumor cell lines (IC50: 15–67 μg/mL) were significantly lower than the values for normal fibroblast cells (IC50: >?100 μg/mL, p < 0.0001) or carmustine (BCNU)-treated tumor cells (IC50: 40 ～ 100 μg/mL, p < 0.001; Table 1). In the two normal cell types, vascular endothelial cells (IC50 = 25.0 ± 2.0 μg/mL) were more sensitive to BP than fibroblast cells (IC50 > 100 μg/mL) (p < 0.0001). These experiments showed that BP could induce high cytotoxicity against brain and other tumour cells but only low or no cytotoxicity against normal fibroblast cells.

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

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