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6066-49-5,MFCD01704513
Catalog No.:AA00E9UW

6066-49-5 | Butylphthalide

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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00E9UW
Chemical Name:
Butylphthalide
CAS Number:
6066-49-5
Molecular Formula:
C12H14O2
Molecular Weight:
190.2384
MDL Number:
MFCD01704513
SMILES:
CCCCC1OC(=O)c2c1cccc2
FEMA Number:
3334
Properties
Properties
 
BP:
312.7°C at 760 mmHg  
Form:
Liquid  
Refractive Index:
1.5197 (estimate)  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
212  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
14  
Hydrogen Bond Acceptor Count:
2  
Rotatable Bond Count:
3  
Undefined Atom Stereocenter Count:
1  
XLogP3:
2.8  

Downstream Synthesis Route

[1]BioorganicandMedicinalChemistryLetters,2011,vol.21,p.4210-4214

[2]BioorganicandMedicinalChemistryLetters,2015,vol.25,p.3535-3540

[3]GazzettaChimicaItaliana,1927,vol.57,p.260

[4]OrganicandBiomolecularChemistry,2011,vol.9,p.5670-5681

[5]OrganicandBiomolecularChemistry,2012,vol.10,p.9030-9040

[6]Patent:CN105884726,2016,A.Locationinpatent:Paragraph0065;0066;0067-0071

[7]Patent:CN106928155,2017,A.Locationinpatent:Paragraph0028;0039

[8]Patent:CN108715579,2018,A

[9]Patent:US2019/375729,2019,A1.Locationinpatent:Paragraph0092

[10]ChineseChemicalLetters,2020

[1]Patent:CN107216298,2017,A.Locationinpatent:Paragraph0063;0064;0065;0073;0074;0075

[2]Patent:CN105884726,2016,A.Locationinpatent:Paragraph0065;0066;0072

[3]AttidellaAccademiaNazionaledeiLincei,ClassediScienzeFisiche,MatematicheeNaturali,Rendiconti,1897,vol.<5>6I,p.369    ChemischeBerichte,1897,vol.30,p.1429

[4]AttidellaAccademiaNazionaledeiLincei,ClassediScienzeFisiche,MatematicheeNaturali,Rendiconti,1897,vol.<5>6I,p.369    ChemischeBerichte,1897,vol.30,p.1429

[5]Patent:CN109081822,2018,A.Locationinpatent:Paragraph0015;0016;0017;0018;0019;0020

[6]Patent:CN109081822,2018,A.Locationinpatent:Paragraph0015;0021

[7]Patent:CN110003154,2019,A.Locationinpatent:Paragraph0056;0058-0059;0052;0054-0056;0060;0062-0063

[1]ChineseChemicalLetters,2019,vol.30,p.725-728

[2]YakugakuZasshi/JournalofthePharmaceuticalSocietyofJapan,1937,vol.57,p.783,788;dtsch.Ref.S.196,199    ChemischesZentralblatt,1937,vol.108,p.4050

[3]HelveticaChimicaActa,1943,vol.26,p.1281,1290

[4]Patent:CN105330631,2016,A.Locationinpatent:Paragraph0023

[5]Patent:CN105968077,2016,A.Locationinpatent:Paragraph0053

[6]Patent:CN108912077,2018,A.Locationinpatent:Paragraph0141-0146

[7]Patent:CN105130934,2018,B.Locationinpatent:Paragraph0081;0084;0085

3413-15-8   
6-nitro-3-n-butylphthalide 

[1]JournalofMolecularandCellularCardiology,2019,vol.135,p.52-66

[2]HelveticaChimicaActa,1943,vol.26,p.1281,1290

[3]BioorganicandMedicinalChemistryLetters,2013,vol.23,p.1985-1988

[4]BioorganicandMedicinalChemistryLetters,2017,vol.27,p.718-722

[1]BioorganicandMedicinalChemistryLetters,2017,vol.27,p.718-722

[2]Tetrahedron,1988,vol.44,p.2903

Literature

Title: Studies on the enantiomers of ZJM-289: synthesis and biological evaluation of antiplatelet, antithrombotic and neuroprotective activities.

Journal: Organic & biomolecular chemistry 20121207

Title: Dl-3-n-butylphthalide and its emerging beneficial effects in neurology.

Journal: Chinese medical journal 20120901

Title: Discovery of a potential anti-ischemic stroke agent: 3-pentylbenzo[c]thiophen-1(3H)-one.

Journal: Journal of medicinal chemistry 20120823

Title: Dl-3-n-butylphthalide, a natural antioxidant, protects dopamine neurons in rotenone models for Parkinson's disease.

Journal: Neurobiology of aging 20120801

Title: DL-3-n-Butylphthalide, an anti-oxidant agent, prevents neurological deficits and cerebral injury following stroke per functional analysis, magnetic resonance imaging and histological assessment.

Journal: Current neurovascular research 20120801

Title: DL-3-n-Butylphthalide protects rat bone marrow stem cells against hydrogen peroxide-induced cell death through antioxidation and activation of PI3K-Akt pathway.

Journal: Neuroscience letters 20120516

Title: Effects of DL-3-n-butylphthalide on vascular dementia and angiogenesis.

Journal: Neurochemical research 20120501

Title: Protection against neurotoxicity by an autophagic mechanism.

Journal: Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas 20120501

Title: Therapeutic effects of dl-3-n-butylphthalide in a transgenic mouse model of amyotrophic lateral sclerosis.

Journal: Chinese medical journal 20120501

Title: dl-3n-Butylphthalide promotes angiogenesis via the extracellular signal-regulated kinase 1/2 and phosphatidylinositol 3-kinase/Akt-endothelial nitric oxide synthase signaling pathways.

Journal: Journal of cardiovascular pharmacology 20120401

Title: DL-3-n-butylphthalide extends survival by attenuating glial activation in a mouse model of amyotrophic lateral sclerosis.

Journal: Neuropharmacology 20120201

Title: (S)-ZJM-289, a nitric oxide-releasing derivative of 3-n-butylphthalide, protects against ischemic neuronal injury by attenuating mitochondrial dysfunction and associated cell death.

Journal: Neurochemistry international 20120101

Title: L-3-n-butylphthalide reduces tau phosphorylation and improves cognitive deficits in AβPP/PS1-Alzheimer's transgenic mice.

Journal: Journal of Alzheimer's disease : JAD 20120101

Title: [Effect of butylphthalide on levels of glutamate and expression of NR2B in the hippocampus of rats with alcohol addiction].

Journal: Zhongguo ying yong sheng li xue za zhi = Zhongguo yingyong shenglixue zazhi = Chinese journal of applied physiology 20120101

Title: The therapeutic effect of (DL)-3-n-butylphthalide in rats with chronic cerebral hypoperfusion through downregulation of amyloid precursor protein and matrix metalloproteinase-2.

Journal: The Journal of international medical research 20120101

Title: Identification of circulatory and excretory metabolites of a novel nitric oxide donor ZJM-289 in rat plasma, bile, urine and faeces by liquid chromatography-tandem mass spectrometry.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20110901

Title: Design, synthesis and evaluation of nitric oxide releasing derivatives of 3-n-butylphthalide as antiplatelet and antithrombotic agents.

Journal: Organic & biomolecular chemistry 20110821

Title: Synthesis and evaluation of nitric oxide-releasing derivatives of 3-n-butylphthalide as anti-platelet agents.

Journal: Bioorganic & medicinal chemistry letters 20110715

Title: 3-n-Butylphthalide (NBP) attenuated neuronal autophagy and amyloid-β expression in diabetic mice subjected to brain ischemia.

Journal: Neurological research 20110501

Title: Antiproliferative effects of essential oil of a compound Chinese herbal medicine Weiqi Decoction on AGS cells.

Journal: Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine 20110501

Title: Chemical composition of the essential oil from kelussia odoratissima Mozaff. and the evaluation of its sedative and anxiolytic effects in mice.

Journal: Clinics (Sao Paulo, Brazil) 20110501

Title: [Studies on the chemical constituents of Ligusticum sinense].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20110301

Title: Novel neuroprotectant chiral 3-n-butylphthalide inhibits tandem-pore-domain potassium channel TREK-1.

Journal: Acta pharmacologica Sinica 20110201

Title: L-3-n-butylphthalide regulates amyloid precursor protein processing by PKC and MAPK pathways in SK-N-SH cells over-expressing wild type human APP695.

Journal: Neuroscience letters 20110107

Title: L-3-n-butyl-phthalide alleviates hydrogen peroxide-induced apoptosis by PKC pathway in human neuroblastoma SK-N-SH cells.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20110101

Title: Discovery of molecular mechanisms of traditional Chinese medicinal formula Si-Wu-Tang using gene expression microarray and connectivity map.

Journal: PloS one 20110101

Title: Asymmetric synthesis and sensory evaluation of sedanenolide.

Journal: Bioscience, biotechnology, and biochemistry 20110101

Title: Bioactivities of major constituents isolated from Angelica sinensis (Danggui).

Journal: Chinese medicine 20110101

Title: [Effects of butylphthalide on the apoptosis of PC-12 cells under the induction of β-amyloid peptide].

Journal: Zhonghua yi xue za zhi 20101207

Title: DL-3-n-butylphthalide prevents neuronal cell death after focal cerebral ischemia in mice via the JNK pathway.

Journal: Brain research 20101104

Title: Protective effect of 3-butyl-6-bromo-1(3H)-isobenzofuranone on hydrogen peroxide-induced damage in PC12 cells.

Journal: Brain research 20101028

Title: [Simultaneous determination of five effective components in Rhizoma Chuanxiong by RP-HPLC].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20101001

Title: [Butylphthalide improves learning and memory abilities of rats with Alzheimer's disease possibly by enhancing protein disulfide isomerase and inhibiting P53 expressions].

Journal: Nan fang yi ke da xue xue bao = Journal of Southern Medical University 20100901

Title: L-3-n-butylphthalide improves cognitive impairment and reduces amyloid-beta in a transgenic model of Alzheimer's disease.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20100616

Title: dl-3-n-Butylphthalide prevents oxidative damage and reduces mitochondrial dysfunction in an MPP(+)-induced cellular model of Parkinson's disease.

Journal: Neuroscience letters 20100514

Title: Synthesis and biological activity of n-butylphthalide derivatives.

Journal: European journal of medicinal chemistry 20100501

Title: 3-n-Butylphthalide (NBP) reduces apoptosis and enhances vascular endothelial growth factor (VEGF) up-regulation in diabetic rats.

Journal: Neurological research 20100501

Title: [Effect of butylphthalide on the expression of GFAP and VEGF in the hippocampus of rats with Alzheimer's disease].

Journal: Zhong nan da xue xue bao. Yi xue ban = Journal of Central South University. Medical sciences 20100201

Title: Synthesis of chiral 3-substituted phthalides by a sequential organocatalytic enantioselective aldol-lactonization reaction. Three-step synthesis of (S)-(-)-3-butylphthalide.

Journal: The Journal of organic chemistry 20100115

Title: Identification and comparative quantification of bio-active phthalides in essential oils from si-wu-tang, fo-shou-san, radix angelica and rhizoma chuanxiong.

Journal: Molecules (Basel, Switzerland) 20100115

Title: [IR and Raman spectroscopic studies on the derivatives of butylphthalide].

Journal: Guang pu xue yu guang pu fen xi = Guang pu 20100101

Title: An efficient system for the asymmetric acylation of (R,S)-3-n-butylphthalide catalyzed by novozyme 435.

Journal: Preparative biochemistry & biotechnology 20100101

Title: Free radical scavenging activities of Cnidium officinale Makino and Ligusticum chuanxiong Hort. methanolic extracts.

Journal: Pharmacognosy magazine 20100101

Title: L-3-n-butylphthalide improves cognitive impairment induced by intracerebroventricular infusion of amyloid-beta peptide in rats.

Journal: European journal of pharmacology 20091025

Title: DL-3-n-butylphthalide protects endothelial cells against oxidative/nitrosative stress, mitochondrial damage and subsequent cell death after oxygen glucose deprivation in vitro.

Journal: Brain research 20090922

Title: Enhanced angiogenesis with dl-3n-butylphthalide treatment after focal cerebral ischemia in RHRSP.

Journal: Brain research 20090915

Title: Identification and determination of the major constituents in Traditional Chinese Medicinal formula Danggui-Shaoyao-San by HPLC-DAD-ESI-MS/MS.

Journal: Journal of pharmaceutical and biomedical analysis 20090908

Title: Simultaneous quantification of active components in the herbs and products of Si-Wu-Tang by high performance liquid chromatography-mass spectrometry.

Journal: Journal of pharmaceutical and biomedical analysis 20090908

Title: [Butylphthalide improves learning and memory abilities of rats with Alzheimer's disease possibly by inhibiting P38 mitogen-activated protein kinase and enhancing extra-cellular signal regulated kinase expressions].

Journal: Nan fang yi ke da xue xue bao = Journal of Southern Medical University 20090801

Title: Long-term treatment of l-3-n-butylphthalide attenuated neurodegenerative changes in aged rats.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20090601

Title: [Effect of butylphthalide on the expression of S100 and glial fibrillary acidic protein in a rat model of Alzheimer disease].

Journal: Nan fang yi ke da xue xue bao = Journal of Southern Medical University 20090601

Title: [Effects of dl-3n-butylphthalide on the expression of VEGF and bFGF in transient middle cerebral artery occlusion rats].

Journal: Sichuan da xue xue bao. Yi xue ban = Journal of Sichuan University. Medical science edition 20090501

Title: Novozyme 435-catalyzed asymmetric acylation of (R, S)-3-n- butylphthalide in hexane.

Journal: Preparative biochemistry & biotechnology 20090101

Title: GC-MS fingerprints for discrimination of Ligusticum chuanxiong from Angelica.

Journal: Journal of separation science 20081001

Title: High-performance liquid chromatography for the determination of 3-n-butylphthalide in rat plasma by tandem quadrupole mass spectrometry: application to a pharmacokinetic study.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080701

Title: [Mechanism of action of butylphalide against the injury following oxygen glucose deprivation/reoxygenation in rat cortical neurons].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20080401

Title: l-3-n-Butylphthalide ameliorates beta-amyloid-induced neuronal toxicity in cultured neuronal cells.

Journal: Neuroscience letters 20080328

Title: [Effects of dl-3-n-butylphthalide on expression of VEGF and bFGF in rat brain with permanent focal cerebral ischemia].

Journal: Sichuan da xue xue bao. Yi xue ban = Journal of Sichuan University. Medical science edition 20080101

Title: Novozyme 435-catalyzed efficient acylation of 3-n-butylphthalide in organic medium.

Journal: Preparative biochemistry & biotechnology 20080101

Title: dl-3n-butylphthalide prevents stroke via improvement of cerebral microvessels in RHRSP.

Journal: Journal of the neurological sciences 20070915

Title: Synthesis, resolution, and antiplatelet activity of 3-substituted 1(3H)-isobenzofuranone.

Journal: Bioorganic & medicinal chemistry letters 20070915

Title: l-3-n-Butylphthalide improves cognitive impairment induced by chronic cerebral hypoperfusion in rats.

Journal: The Journal of pharmacology and experimental therapeutics 20070601

Title: [The effect of butylphthalide on expression of NGF and BDNF in ischemia stroke tissue of rat cerebrum].

Journal: Sichuan da xue xue bao. Yi xue ban = Journal of Sichuan University. Medical science edition 20070601

Title: 2-(1-Hydroxypentyl)-benzoate increases cerebral blood flow and reduces infarct volume in rats model of transient focal cerebral ischemia.

Journal: The Journal of pharmacology and experimental therapeutics 20060601

Title: Live cell extraction and HPLC-MS analysis for predicting bioactive components of traditional Chinese medicines.

Journal: Journal of pharmaceutical and biomedical analysis 20060503

Title: Potent odorants characterize the aroma quality of leaves and stalks in raw and boiled celery.

Journal: Bioscience, biotechnology, and biochemistry 20060401

Title: Characterization of interaction property of multicomponents in Chinese Herb with protein by microdialysis combined with HPLC.

Journal: Analytica chimica acta 20060118

Title: Development of high-performance liquid chromatographic fingerprints for distinguishing Chinese Angelica from related umbelliferae herbs.

Journal: Journal of chromatography. A 20050506

Title: Synthesis of enantiopure phthalides including 3-butylphthalide, a fragrance component of celery oil, and determination of their absolute configurations.

Journal: Chirality 20050505

Title: HPLC-coupled spectroscopic techniques (UV, MS, NMR) for the structure elucidation of phthalides in Ligusticum chuanxiong.

Journal: Molecular diversity 20050101

Title: [Preparation of covalently bonded cellulose tris (4-methylbenzoate) derivative chiral stationary phases through a polymerization reaction].

Journal: Se pu = Chinese journal of chromatography 20041101

Title: Recent pharmacological studies on natural products in China.

Journal: European journal of pharmacology 20041001

Title: Antiplatelet and antithrombotic activity of L-3-n-butylphthalide in rats.

Journal: Journal of cardiovascular pharmacology 20040601

Title: Determination of 3-n-butylphthalide in rabbit plasma by HPLC with fluorescence detection and its application in pharmacokinetic study.

Journal: Biomedical chromatography : BMC 20030901

Title: Effects of chiral 3-n-butylphthalide on apoptosis induced by transient focal cerebral ischemia in rats.

Journal: Acta pharmacologica Sinica 20030801

Title: Simultaneous analysis of seventeen chemical ingredients of Ligusticum chuanxiong by on-line high performance liquid chromatography-diode array detector-mass spectrometry.

Journal: Planta medica 20030501

Title: Synthesis of phthalides and 3,4-dihydroisocoumarins using the palladium-catalyzed intramolecular benzannulation strategy.

Journal: The Journal of organic chemistry 20020419

Title: Separation and identification of the phthalic anhydride derivatives of Liqusticum Chuanxiong Hort by GC-MS, TLC, HPLC-DAD, and HPLC-MS.

Journal: Journal of chromatographic science 20020301

Title: [Effects of NBP on ATPase and anti-oxidant enzymes activities and lipid peroxidation in transient focal cerebral ischemic rats].

Journal: Zhongguo yi xue ke xue yuan xue bao. Acta Academiae Medicinae Sinicae 20020201

Title: New drugs derived from medicinal plants.

Journal: Therapie 20020101

Title: [Effects of 3-n-butylphthalide on thrombosis formation and platelet function in rats].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20010501

Title: Cui LY, et al. Ninety-day administration of dl-3-n-butylphthalide for acute ischemic stroke: a randomized, double-blind trial. Chin Med J (Engl). 2013;126(18):3405-10.

Title: Zhao W, et al. 3-N-butylphthalide improves neuronal morphology after chronic cerebral ischemia. Neural Regen Res. 2014 Apr 1;9(7):719-26.

Title: Wang X, et al. Design, synthesis and biological evaluation of hydrogen sulfide releasing derivatives of 3-n-butylphthalide as potential antiplatelet and antithrombotic agents. Org Biomol Chem. 2014 Aug 21;12(31):5995-6004.

Title: Wang F, et al. Improvement of cognitive deficits in SAMP8 mice by 3-n-butylphthalide. Neurol Res. 2014 Mar;36(3):224-33.

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Tags:6066-49-5 Molecular Formula|6066-49-5 MDL|6066-49-5 SMILES|6066-49-5 Butylphthalide