Butylphthalide

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.^[1]

Quick facts Names, Identifiers ...

Butylphthalide

Names
Preferred IUPAC name 3-Butyl-2-benzofuran-1(3H)-one
Other names 3-Butylphthalide; 3-n-Butylphthalide
Identifiers
CAS Number	6066-49-5 Y
3D model (JSmol)	Interactive image
Abbreviations	NBP; BuPh
ChemSpider	55293
ECHA InfoCard	100.025.455
PubChem CID	61361
UNII	822Q956KGM
CompTox Dashboard (EPA)	DTXSID50863687
InChI InChI=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 Key: HJXMNVQARNZTEE-UHFFFAOYSA-N 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 Key: HJXMNVQARNZTEE-UHFFFAOYAC
SMILES O=C1OC(c2ccccc12)CCCC
Properties
Chemical formula	C12H14O2
Molar mass	190.242 g·mol−1
Appearance	clear oily liquid
Related compounds
Related compounds	Phthalide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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Studies in animal models suggest that butylphthalide may be useful for the treatment of hypertension^[2][3] and may have neuroprotective effects.^[4][5][6][7] In 2002, NBP was approved in China for the treatment of cerebral ischemia.^[8]

NBP undergoes extensive metabolism in humans.^[9] 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.^[10]