WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 319640
CAS#: 6066-49-5
Description: Butylphthalide, also known as 3-n-butylphthalide or NBP, is an antioxidant and one of the chemical constituents in celery oil, along with sedanolide, which is primarily responsible for the aroma and taste of celery. Butylphthalide may be useful for the treatment of hypertension and may have neuroprotective effects. In 2004, NBP was approved in China for the treatment of cerebral ischemia. Minor side effects were observed in preclinical and clinical studies. The minor bioactivation pathway of NBP was proved to be medicated via sulfation of 3-OH-NBP.
MedKoo Cat#: 319640
Name: Butylphthalide
CAS#: 6066-49-5
Chemical Formula: C12H14O2
Exact Mass: 190.0994
Molecular Weight: 190.242
Elemental Analysis: C, 75.76; H, 7.42; O, 16.82
Synonym: Butylphthalide; 3-n-Butylphthalide; N-butylphthalide; NBP; DL-3-n-butylphthalide; rac-3-n-butylphthalide.
IUPAC/Chemical Name: 3-Butyl-2-benzofuran-1(3H)-one
InChi Key: HJXMNVQARNZTEE-UHFFFAOYSA-N
InChi Code: 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
SMILES Code: O=C1OC(CCCC)C2=CC=CC=C12
1: Zhao H, Yun W, Zhang Q, Cai X, Li X, Hui G, Zhou X, Ni J. Mobilization of Circulating Endothelial Progenitor Cells by dl-3-n-Butylphthalide in Acute Ischemic Stroke Patients. J Stroke Cerebrovasc Dis. 2016 Jan 13. pii: S1052-3057(15)00629-1. doi: 10.1016/j.jstrokecerebrovasdis.2015.11.018. [Epub ahead of print] PubMed PMID: 26775268.
2: Jiang Y, Sun L, Xuan X, Wang J. Impacts of N-Butylphthalide on expression of growth factors in rats with focal cerebral ischemia. Bosn J Basic Med Sci. 2016 Jan 1. doi: 10.17305/bjbms.2016.560. [Epub ahead of print] PubMed PMID: 26773175.
3: Wang F, Ma J, Han F, Guo X, Meng L, Sun Y, Jin C, Duan H, Li H, Peng Y. DL-3-n-butylphthalide delays the onset and progression of diabetic cataract by inhibiting oxidative stress in rat diabetic model. Sci Rep. 2016 Jan 13;6:19396. doi: 10.1038/srep19396. PubMed PMID: 26759189.
4: Zhao CY, Lei H, Zhang Y, Li L, Xu SF, Cai J, Li PP, Wang L, Wang XL, Peng Y. L-3-n-Butylphthalide attenuates neuroinflammatory responses by downregulating JNK activation and upregulating Heme oxygenase-1 in lipopolysaccharide-treated mice. J Asian Nat Prod Res. 2015 Dec 16:1-14. [Epub ahead of print] PubMed PMID: 26675131.
5: Hu Y, Bi X, Zhao P, Zheng H, Huang X. Cytotoxic Activities, SAR and Anti-Invasion Effects of Butylphthalide Derivatives on Human Hepatocellular Carcinoma SMMC7721 Cells. Molecules. 2015 Nov 12;20(11):20312-9. doi: 10.3390/molecules201119699. PubMed PMID: 26569212.
6: Diao XX, Zhong K, Li XL, Zhong DF, Chen XY. Isomer-selective distribution of 3-n-butylphthalide (NBP) hydroxylated metabolites, 3-hydroxy-NBP and 10-hydroxy-NBP, across the rat blood-brain barrier. Acta Pharmacol Sin. 2015 Dec;36(12):1520-7. doi: 10.1038/aps.2015.64. Epub 2015 Nov 16. PubMed PMID: 26567730.
7: Du R, Teng JF, Wang Y, Zhao XY, Shi ZB. Clinical study of Butylphthalide combined with Xue Shuan Tong on serum inflammatory factors and prognosis effect of patients with cerebral infarction. Pak J Pharm Sci. 2015 Sep;28(5 Suppl):1823-7. PubMed PMID: 26525022.
8: Zhou Y, Niu LJ, Qi FM, Guo L. [Effect of 3-n-butylphthalide pretreatment on expression of the HSP70 after brain ischemia/reperfusion]. Zhongguo Ying Yong Sheng Li Xue Za Zhi. 2015 Mar;31(2):136-40. Chinese. PubMed PMID: 26248419.
9: Zhao Q, Hu JP, Jiang J, Li Y, Hu P. [Interaction of butylphthalide with rat and human liver CYP450 isoenzymes]. Yao Xue Xue Bao. 2015 May;50(5):541-6. Chinese. PubMed PMID: 26234133.
10: Yang LC, Li J, Xu SF, Cai J, Lei H, Liu DM, Zhang M, Rong XF, Cui DD, Wang L, Peng Y, Wang XL. L-3-n-butylphthalide Promotes Neurogenesis and Neuroplasticity in Cerebral Ischemic Rats. CNS Neurosci Ther. 2015 Sep;21(9):733-41. doi: 10.1111/cns.12438. Epub 2015 Jul 28. PubMed PMID: 26215907.
11: Sheng X, Hua K, Yang C, Wang X, Ji H, Xu J, Huang Z, Zhang Y. Novel hybrids of 3-n-butylphthalide and edaravone: Design, synthesis and evaluations as potential anti-ischemic stroke agents. Bioorg Med Chem Lett. 2015 Sep 1;25(17):3535-40. doi: 10.1016/j.bmcl.2015.06.090. Epub 2015 Jul 3. PubMed PMID: 26189079.
12: Wu Y, Huang Q, Liu X, Wei X. Dl-3-n-butylphthalide is effective for demyelination: a case-combined study. Clin Neurol Neurosurg. 2015 Oct;137:83-8. doi: 10.1016/j.clineuro.2015.06.024. Epub 2015 Jul 2. PubMed PMID: 26164676.
13: Jia J, Wei C, Liang J, Zhou A, Zuo X, Song H, Wu L, Chen X, Chen S, Zhang J, Wu J, Wang K, Chu L, Peng D, Lv P, Guo H, Niu X, Chen Y, Dong W, Han X, Fang B, Peng M, Li D, Jia Q, Huang L. The effects of DL-3-n-butylphthalide in patients with vascular cognitive impairment without dementia caused by subcortical ischemic small vessel disease: A multicentre, randomized, double-blind, placebo-controlled trial. Alzheimers Dement. 2015 Jun 15. pii: S1552-5260(15)00193-4. doi: 10.1016/j.jalz.2015.04.010. [Epub ahead of print] PubMed PMID: 26086183.
14: Hua K, Sheng X, Li TT, Wang LN, Zhang YH, Huang ZJ, Ji H. The edaravone and 3-n-butylphthalide ring-opening derivative 10b effectively attenuates cerebral ischemia injury in rats. Acta Pharmacol Sin. 2015 Aug;36(8):917-27. doi: 10.1038/aps.2015.31. Epub 2015 Jun 15. PubMed PMID: 26073328; PubMed Central PMCID: PMC4564877.
15: Li Q, Cheng Y, Bi M, Lin H, Chen Y, Zou Y, Liu Y, Kang H, Guo Y. Effects of N-butylphthalide on the activation of Keap1/Nrf-2 signal pathway in rats after carbon monoxide poisoning. Environ Toxicol Pharmacol. 2015 Jul;40(1):22-9. doi: 10.1016/j.etap.2015.05.009. Epub 2015 May 22. PubMed PMID: 26056974.
16: Zhang W, Tan N, Jia X, Wang G, Long W, Li X, Liao S, Hou D. Synthesis, recognition characteristics and properties of l-3-n-butylphthalide molecularly imprinted polymers as sorbent for solid-phase extraction through precipitation polymerization. Mater Sci Eng C Mater Biol Appl. 2015 Aug;53:166-74. doi: 10.1016/j.msec.2015.04.034. Epub 2015 Apr 25. PubMed PMID: 26042704.
17: Li Q, Cheng Y, Bi MJ, Kang H, Qu Y, Lin H, Guo Y, Zou Y. Effects of N-Butylphthalide on the expressions of Nogo/NgR in rat brain tissue after carbon monoxide poisoning. Environ Toxicol Pharmacol. 2015 Mar;39(2):953-61. doi: 10.1016/j.etap.2015.02.013. Epub 2015 Feb 26. PubMed PMID: 25812770.
18: Ye J, Zhai L, Zhang S, Zhang Y, Chen L, Hu L, Zhang S, Ding Z. DL-3-n-butylphthalide inhibits platelet activation via inhibition of cPLA2-mediated TXA2 synthesis and phosphodiesterase. Platelets. 2015;26(8):736-44. doi: 10.3109/09537104.2014.989826. Epub 2015 Mar 3. PubMed PMID: 25734213.
19: Li Y, Zhao L, Li X, Guo B, Zhao J, Wang X, Zhang T. Quantification of 3-n-butylphthalide in beagle plasma samples by supercritical fluid chromatography with triple quadruple mass spectrometry and its application to an oral bioavailability study. J Sep Sci. 2015 Feb;38(4):697-702. doi: 10.1002/jssc.201401073. Epub 2015 Jan 7. PubMed PMID: 25446715.
20: Zhu J, Zhang Y, Yang C. Protective effect of 3-n-butylphthalide against hypertensive nephropathy in spontaneously hypertensive rats. Mol Med Rep. 2015 Feb;11(2):1448-54. doi: 10.3892/mmr.2014.2791. Epub 2014 Oct 27. PubMed PMID: 25352064.
