{{Chembox | ImageFile = Butylphthalide.svg | ImageSize = 200px | PIN = 3-Butyl-2-benzofuran-1(3''H'')-one | OtherNames = 3-Butylphthalide; 3-''n''-Butylphthalide |Section1={{Chembox Identifiers | Abbreviations = NBP; BuPh | CASNo = 6066-49-5 | CASNo_Ref = {{cascite|correct|}} | UNII = 822Q956KGM | PubChem = 61361 | ChemSpiderID = 55293 | SMILES = O=C1OC(c2ccccc12)CCCC | InChI = 1/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-7,11H,2-3,8H2,1H3 | InChIKey = HJXMNVQARNZTEE-UHFFFAOYAC | StdInChI = 1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-7,11H,2-3,8H2,1H3 | StdInChIKey = HJXMNVQARNZTEE-UHFFFAOYSA-N }} |Section2={{Chembox Properties | C=12 | H=14 | O=2 | Appearance = clear oily liquid | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} |Section8={{Chembox Related | OtherFunction = | OtherFunction_label = | OtherCompounds = Phthalide}} }}
'''Butylphthalide''' ('''3-''n''-butylphthalide''' or '''NBP''') is one of the chemical constituents in celery oil, along with sedanolide, which is primarily responsible for the aroma and taste of celery.<ref>{{cite journal | title = Relative recovery and identification of carbonyl compounds from celery essential oil | author = Wilson, Charles Welthy III | journal = Journal of Food Science | year = 1970 | volume = 35 | issue = 6 | pages = 766–768 | doi = 10.1111/j.1365-2621.1970.tb01989.x}}</ref>
Studies in animal models suggest that butylphthalide may be useful for the treatment of hypertension<ref>{{cite journal | doi = 10.1016/j.pcad.2005.01.004 | title = Nutraceuticals, Vitamins, Antioxidants, and Minerals in the Prevention and Treatment of Hypertension | year = 2005 | last1 = Houston | first1 = M | journal = Progress in Cardiovascular Diseases | volume = 47 | issue = 6 | pages = 396–449 | pmid = 16115519}}</ref><ref>{{cite journal | title = Cardiovascular Pharmacology of 3-n-butylphthalide in Spontaneously Hypertensive Rats | author = D. Tsi and B. K. H. Tan | journal = Phytotherapy Research | volume = 11 | pages = 576–582 | year = 1997 | doi = 10.1002/(SICI)1099-1573(199712)11:8<576::AID-PTR174>3.0.CO;2-7 | issue = 8| s2cid = 73033504 | doi-access = free }}</ref> and may have neuroprotective effects.<ref>{{cite journal | pmid = 22056419 | year = 2011 | last1 = Feng | first1 = X | last2 = Peng | first2 = Y | last3 = Liu | first3 = M | last4 = Cui | first4 = L | title = Dl-3-n-butylphthalide extends survival by attenuating glial activation in a mouse model of amyotrophic lateral sclerosis | doi = 10.1016/j.neuropharm.2011.10.009 | journal = Neuropharmacology | volume=62 | issue=2 | pages=1004–10| s2cid = 37504365 }}</ref><ref>{{cite journal | pmid = 21535939 | year = 2011 | last1 = Zhang | first1 = T | last2 = Yan | first2 = W | last3 = Li | first3 = Q | last4 = Fu | first4 = J | last5 = Liu | first5 = K | last6 = Jia | first6 = W | last7 = Sun | first7 = X | last8 = Liu | first8 = X | title = 3-n-butylphthalide (NBP) attenuated neuronal autophagy and amyloid-beta expression in diabetic mice subjected to brain ischemia | volume = 33 | issue = 4 | pages = 396–404 | doi = 10.1179/1743132810Y.0000000006 | journal = Neurological Research| s2cid = 35636793 }}</ref><ref>{{cite journal | pmid = 21293470 | year = 2011 | last1 = Ji | first1 = XC | last2 = Zhao | first2 = WH | last3 = Cao | first3 = DX | last4 = Shi | first4 = QQ | last5 = Wang | first5 = XL | title = Novel neuroprotectant chiral 3-n-butylphthalide inhibits tandem-pore-domain potassium channel TREK-1 | volume = 32 | issue = 2 | pages = 182–7 | doi = 10.1038/aps.2010.210 | journal = Acta Pharmacologica Sinica| pmc = 4009930 }}</ref><ref>{{cite journal | pmid = 21524431 | year = 2011 | last1 = Xiong | first1 = N | last2 = Huang | first2 = J | last3 = Chen | first3 = C | last4 = Zhao | first4 = Y | last5 = Zhang | first5 = Z | last6 = Jia | first6 = M | last7 = Zhang | first7 = Z | last8 = Hou | first8 = L | last9 = Yang | first9 = H | title = Dl-3-n-butylphthalide, a natural antioxidant, protects dopamine neurons in rotenone models for Parkinson's disease | doi = 10.1016/j.neurobiolaging.2011.03.007 | journal = Neurobiology of Aging| last10 = Cao | first10 = Xuebing | last11 = Liang | first11 = Zhihou | last12 = Zhang | first12 = Yongxue | last13 = Sun | first13 = Shenggang | last14 = Lin | first14 = Zhicheng | last15 = Wang | first15 = Tao | volume = 33 | issue = 8 | pages = 1777–91 | s2cid = 27840652 }}</ref> In 2002, NBP was approved in China for the treatment of cerebral ischemia.<ref>{{cite journal |pmc=5178327|year=2016|last1=Abdoulaye|first1=I. A.|title=A Review of Recent Advances in Neuroprotective Potential of 3-N-Butylphthalide and Its Derivatives|journal=BioMed Research International|volume=2016|article-number=5012341|last2=Guo|first2=Y. J.|doi=10.1155/2016/5012341|pmid=28053983|doi-access=free}}</ref>
NBP undergoes extensive metabolism in humans.<ref>Diao X, Deng P, Xie C, Li X, Zhong D, Zhang Y, Chen X. Metabolism and pharmacokinetics of 3-n-butylphthalide (NBP) in humans: the role of cytochrome P450s and alcohol dehydrogenase in biotransformation. Drug Metab Dispos 2013;41:430-444.</ref> The major metabolites in human plasma were 3-OH-NBP, 10-OH-NBP, 10-CO-NBP, 11-COOH-NBP. The AUC of metabolites was much larger than that of NBP.
Minor side effects were observed in preclinical and clinical studies. The minor bioactivation pathway of NBP was proved to be mediated via sulfation of 3-OH-NBP.<ref>Diao X, Pang X, Xie C, Guo Z, Zhong D, Chen X. Bioactivation of 3-n-butylphthalide via sulfation of its major metabolite 3-hydroxy-NBP: mediated mainly by sulfotransferase 1A1. Drug Metab Dispos 2014;42:774-781.</ref>
==References== {{reflist}}
Category:Phthalides Category:Flavors Category:Celery