N-BUTYLIDENEPHTHALIDE

N-BUTYLIDENEPHTHALIDE Basic information
Description Reference
Product Name:N-BUTYLIDENEPHTHALIDE
Synonyms: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
CAS:551-08-6
MF:C12H12O2
MW:188.22
EINECS:208-991-3
Product Categories:Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;Phthalides;A-B;Alphabetical Listings;Flavors and Fragrances;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
Mol File:551-08-6.mol
N-BUTYLIDENEPHTHALIDE Structure
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.)
FEMA 3333 | 3-BUTYLIDENEPHTHALIDE
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
Odorat 10.00 % in dipropylene glycol. herbal lovage celery
Odor Typeherbal
JECFA Number1170
BRN 5145
InChIKeyWMBOCUXXNSOQHM-FLIBITNWSA-N
LogP3.72
CAS DataBase Reference551-08-6(CAS DataBase Reference)
EPA Substance Registry System1(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 Information
ProviderLanguage
SigmaAldrich English
ALFA English
N-BUTYLIDENEPHTHALIDE Usage And Synthesis
DescriptionN-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 Properties3-Butylidenephthalide has a pervasive warm spicy aroma.
OccurrenceReported as occurring naturally in the fruits and roots of Ligusticum acutilobum and lovage (Levisticum officinale) seeds, roots and leaves.
Uses3-Butylidenephthalide is a phthalide derivative useful for control of sensation disorder and olfaction disorder.
DefinitionChEBI: A gamma-lactone that is phthalide substituted by a butylidene group at position 3. Isolated from Ligusticum porteri, it exhibits hypoglycemic activity.
Taste threshold valuesTaste characteristics at 15 ppm: celery, green, vegetable-like with a herbal nuance.
General Description3-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 ProfileModerately toxic by ingestion. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
targetNrf2 | TNF-α | NO | IL Receptor
N-BUTYLIDENEPHTHALIDE Preparation Products And Raw materials
Raw materials3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonic acid-->Phthalic anhydride-->VALERIC ANHYDRIDE-->Butyraldehyde
Preparation Products1(3H)-Isobenzofuranone, 3-butylhexahydro-
1-BUTENE ethylidene phthalide ISOBUTANE 3-N-BUTYLPHTHALIDE Butylphthalide impurity ZINC TELLURIDE MONOBUTYL PHTHALATE 1(3H)-Isobenzofuranone,3-methyl-(9CI) Butylphthalide impurity Morpholine Amlodipine 2-Acetylbenzoic acid Palmitic acid ethyl ester N-BUTYLIDENEPHTHALIDE 3-(Z)-(PENTAFLUOROPROPIONYLMETHYLENE)PHTHALIDE Phthalide FEMA 2952 VINYL BENZOATE

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