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3-Butylidenephthalide

Description Reference
Product Name
3-Butylidenephthalide
CAS No.
551-08-6
Chemical Name
3-Butylidenephthalide
Synonyms
3-BUTYLIDENEPHTHALIDE;Bdph;BUTYLIDENE PHTHALIDE;3-butylidene-phthalid;3-Butylideneisobenzofuran-1(3H)-one;FEMA 3333;Ai3-37306;NSC 325307;Einecs 208-991-3;Butenylphthalide
CBNumber
CB0173298
Molecular Formula
C12H12O2
Formula Weight
188.22
MOL File
551-08-6.mol
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3-Butylidenephthalide Property

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)
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Safety

Hazard Codes 
Xn
Risk Statements 
22
Safety Statements 
23
WGK Germany 
2
RTECS 
TI3692500
TSCA 
Yes
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P330Rinse mouth.

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N-Bromosuccinimide Price

Alfa Aesar
Product number
A10353
Product name
n-Butylidenephthalide, (E)+(Z), 95%
Packaging
10g
Price
$31.65
Updated
2024/03/01
Alfa Aesar
Product number
A10353
Product name
n-Butylidenephthalide, (E)+(Z), 95%
Packaging
50g
Price
$90.65
Updated
2024/03/01
Alfa Aesar
Product number
A10353
Product name
n-Butylidenephthalide, (E)+(Z), 95%
Packaging
250g
Price
$342
Updated
2023/06/20
Usbiological
Product number
299818
Product name
3-Butylidenephthalide
Packaging
20mg
Price
$297
Updated
2021/12/16
TRC
Product number
B692250
Product name
3-ButylidenePhthalide(CisTransmixture)
Packaging
25g
Price
$425
Updated
2021/12/16
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3-Butylidenephthalide Chemical Properties,Usage,Production

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

3-Butylidenephthalide Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 3-Butylidenephthalide manufacturers

Hebei Zhuanglai Chemical Trading Co Ltd
Product
3-Butylidene phthalide 551-08-6
Price
US $45.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20 tons
Release date
2024-12-12
Shijiazhuang Dowell Chemical Co.,Ltd
Product
3-Butylidene phthalide 551-08-6
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
500kg/month
Release date
2024-12-03
Hebei Weibang Biotechnology Co., Ltd
Product
N-BUTYLIDENEPHTHALIDE 551-08-6
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-18

551-08-6, 3-ButylidenephthalideRelated Search:


  • N-BUTYLIDENEPHTHALIDE
  • 3-BUTYLIDENEPHTHALIDE
  • FEMA 3333
  • BUTYLIDENE PHTHALIDE
  • 1(3H)-Isobenzofuranone,3-butylidene-
  • 3-butylidene-1(3h)-isobenzofuranon
  • 3-butylidene-1(3H)-Isobenzofuranone
  • 3-butylidene-phthalid
  • 3-BUTYLIDENEPHTHALIDE 96+%
  • n-Butylidenephthalide,95%
  • 3-Butylidene-1,3-dihydroisobenzofuran-1-one
  • 3-Butylideneisobenzofuran-1(3H)-one
  • n-Butylidenephthalide, (E)+(Z), 95%
  • ligusticumlactone
  • 3-Butylidene phthalide - mixture ofcisandtransisomers
  • Butylphthalide Impurity 2
  • 3-Butylidene Phthalide (Cis Trans Mixture)
  • (Z)-3-butylidenephthalide
  • Phthalide,3-butylidene-(6CI,7CI,8CI)
  • Butylphthalide Impurity 23
  • NSC 325307
  • Ai3-37306
  • Bdph
  • Einecs 208-991-3
  • n-Butylidenephthalide, E- and Z-, 95%
  • 3-Butylphthalide Impurity 21
  • Butyphthalide impurity 20
  • 3-Butylidenphthalid
  • Butenylphthalide
  • N-BUTYLIDENEPHTHALID
  • 3-butyidenephthalide
  • BUTYLIDENE PTHALIDE
  • 3-n-butenylphthalide
  • (3E)-3-butylidene-2-benzofuran-1-one
  • Butylphthalide Impurity 27 (mixture of cis and trans isomers)
  • Butylphthalein impurity 20
  • 551-08-6
  • 555-08-6
  • 0551-08-06
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  • reference standards from Chinese medicinal herbs (TCM).
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  • Phthalides