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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
Molecular Weight:
188.22
MDL Number:
MFCD00047319
MOL File:
551-08-6.mol
MSDS File:
SDS
Last updated:2025-01-27 09:38:02

3-Butylidenephthalide Properties

Melting point 82.5°C
Boiling point 139-142 °C/5 mmHg (lit.)
Density 1.103 g/mL at 25 °C (lit.)
FEMA 3333 | 3-BUTYLIDENEPHTHALIDE
refractive index n20/D 1.577(lit.)
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
biological source synthetic
JECFA Number 1170
BRN 5145
InChIKey WMBOCUXXNSOQHM-FLIBITNWSA-N
LogP 3.72
Substances Added to Food (formerly EAFUS) 3-BUTYLIDENEPHTHALIDE
CAS DataBase Reference 551-08-6(CAS DataBase Reference)
FDA UNII S9178G4B3F
EPA Substance Registry System 1(3H)-Isobenzofuranone, 3-butylidene- (551-08-6)
UNSPSC Code 12164502
NACRES NA.21

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312a-P330-P501a
Hazard Codes  Xn
Risk Statements  22
Safety Statements  23
WGK Germany  2
RTECS  TI3692500
TSCA  Yes
NFPA 704
1
2 0

3-Butylidenephthalide price More Price(24)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Alfa Aesar A10353 n-Butylidenephthalide, (E)+(Z), 95% 551-08-6 10g $31.65 2024-03-01 Buy
Alfa Aesar A10353 n-Butylidenephthalide, (E)+(Z), 95% 551-08-6 50g $90.65 2024-03-01 Buy
Alfa Aesar A10353 n-Butylidenephthalide, (E)+(Z), 95% 551-08-6 250g $342 2023-06-20 Buy
Usbiological 299818 3-Butylidenephthalide 551-08-6 20mg $297 2021-12-16 Buy
TRC B692250 3-ButylidenePhthalide(CisTransmixture) 551-08-6 25g $425 2021-12-16 Buy
Product number Packaging Price Buy
A10353 10g $31.65 Buy
A10353 50g $90.65 Buy
A10353 250g $342 Buy
299818 20mg $297 Buy
B692250 25g $425 Buy

3-Butylidenephthalide Chemical Properties,Uses,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

85-44-9
2082-59-9
551-08-6
Synthesis of 3-Butylidenephthalide from Phthalic anhydride and VALERIC ANHYDRIDE

3-Butylidenephthalide Preparation Products And Raw materials

Global( 307)Suppliers
Supplier Tel Email Country ProdList Advantage
Shijiazhuang Dowell Chemical Co.,Ltd
+86-0311-89805679 +8613463963265 sell@dowechem.com China 76 58
career henan chemical co
+86-0371-86658258 +8613203830695 sales@coreychem.com China 29879 58
Hebei Weibang Biotechnology Co., Ltd
+8615531157085 abby@weibangbio.com China 8806 58
Hebei Mujin Biotechnology Co.,Ltd
+86 13288715578 +8613288715578 sales@hbmojin.com China 12831 58
Hebei Zhuanglai Chemical Trading Co Ltd
+86-16264648883 +86-16264648883 niki@zlchemi.com China 3712 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21634 55
Shanghai Zheyan Biotech Co., Ltd.
18017610038 zheyansh@163.com CHINA 3619 58
Chengdu Greenpure Biopharma CO.,Ltd
18283602253; +8618283602253 jancyzheng@gcgreenpure.com China 953 58
Shenzhen Nexconn Pharmatechs Ltd
+86-755-89396905 +86-15013857715 admin@nexconn.com China 10311 58
Chengdu Biopurify Phytochemicals Ltd.
+8618080483897 sales@biopurify.com China 3772 58

View Lastest Price from 3-Butylidenephthalide manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
 3-Butylidene phthalide pictures 2025-01-24 3-Butylidene phthalide
551-08-6
US $45.00 / kg 1kg 99% 20 tons Hebei Zhuanglai Chemical Trading Co Ltd
3-Butylidene phthalide pictures 2025-01-23 3-Butylidene phthalide
551-08-6
US $0.00-0.00 / kg 1kg 99% 500kg/month Shijiazhuang Dowell Chemical Co.,Ltd
3-Butylidenephthalide pictures 2024-11-19 3-Butylidenephthalide
551-08-6
US $31.00-76.00 / mg 90.76% 10g TargetMol Chemicals Inc.
N-BUTYLIDENEPHTHALIDE FEMA 3333 1(3H)-Isobenzofuranone,3-butylidene- 3-butylidene-1(3h)-isobenzofuranon 3-butylidene-1(3H)-Isobenzofuranone 3-BUTYLIDENEPHTHALIDE 96+% n-Butylidenephthalide,95% 3-Butylidene-1,3-dihydroisobenzofuran-1-one n-Butylidenephthalide, (E)+(Z), 95% ligusticumlactone 3-Butylidene Phthalide (Cis Trans Mixture) (Z)-3-butylidenephthalide Phthalide,3-butylidene-(6CI,7CI,8CI) NSC 325307 Ai3-37306 Einecs 208-991-3 n-Butylidenephthalide, E- and Z-, 95% 3-Butylidene phthalide - mixture ofcisandtransisomers Butylphthalide Impurity 2 Butylphthalide Impurity 23 3-Butylphthalide Impurity 21 Butyphthalide impurity 20 3-Butylidenphthalid Butenylphthalide N-BUTYLIDENEPHTHALID BUTYLIDENE PTHALIDE 3-butyidenephthalide 3-n-butenylphthalide (3E)-3-butylidene-2-benzofuran-1-one 3-BUTYLIDENEPHTHALIDE BUTYLIDENE PHTHALIDE 3-butylidene-phthalid 3-Butylideneisobenzofuran-1(3H)-one Bdph Butylphthalide Impurity 27 (mixture of cis and trans isomers) Butylphthalein impurity 20 3-Butylidenephthalide, 10 mM in DMSO 551-08-6 555-08-6 0551-08-06 Aromatics Heterocycles Intermediates & Fine Chemicals Pharmaceuticals chemical reagent pharmaceutical intermediate phytochemical reference standards from Chinese medicinal herbs (TCM). standardized herbal extract A-B Alphabetical Listings Flavors and Fragrances Phthalides