| Identification | More | [Name]
N-BUTYLIDENEPHTHALIDE | [CAS]
551-08-6 | [Synonyms]
3-BUTYLIDENEPHTHALIDE
BUTYLIDENE PHTHALIDE
FEMA 3333
N-BUTYLIDENEPHTHALIDE
1(3H)-Isobenzofuranone,3-butylidene-
3-butylidene-1(3h)-isobenzofuranon
3-butylidene-1(3H)-Isobenzofuranone
3-butylidene-phthalid
ligusticumlactone
3-BUTYLIDENEPHTHALIDE 96+%
n-Butylidenephthalide,95%
n-Butylidenephthalide, (E)+(Z), 95%
3-Butylidene-1,3-dihydroisobenzofuran-1-one
3-Butylideneisobenzofuran-1(3H)-one | [EINECS(EC#)]
208-991-3 | [Molecular Formula]
C12H12O2 | [MDL Number]
MFCD00047319 | [Molecular Weight]
188.22 | [MOL File]
551-08-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
82.5°C | [Boiling point ]
139-142 °C/5 mmHg (lit.) | [density ]
1.103 g/mL at 25 °C(lit.)
| [FEMA ]
3333 | [refractive index ]
n20/D 1.577(lit.)
| [Fp ]
>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 | [biological source]
synthetic | [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 Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) . | [WGK Germany ]
2
| [RTECS ]
TI3692500
| [TSCA ]
Yes | [Safety Profile]
Moderately toxic by
ingestion. A skin irritant. When heated to
decomposition it emits acrid smoke and
irritating fumes. |
| Questions And Answer | Back Directory | [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.
|
| Hazard Information | Back Directory | [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. | [target]
Nrf2 | TNF-α | NO | IL Receptor |
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