Ligustilide | CAS#4431-01-0 | anti-inflammatory

MedKoo Cat#: 584580 | Name: Ligustilide

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ligustilide is a major component of Angelica sinensis and is reported to have anti-inflammatory and neuroprotective effect.

Chemical Structure

Ligustilide

CAS#4431-01-0

Theoretical Analysis

MedKoo Cat#: 584580

Name: Ligustilide

CAS#: 4431-01-0

Chemical Formula: C12H14O2

Exact Mass: 190.0994

Molecular Weight: 190.24

Elemental Analysis: C, 75.76; H, 7.42; O, 16.82

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 350.00	2 Weeks
100mg	USD 850.00	2 Weeks

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Related CAS #

81944-09-4 (Z Isomer) 81944-08-3 (E-isomer) 4431-01-0

Synonym

Ligustilide

IUPAC/Chemical Name

1(3H)-Isobenzofuranone, 3-butylidene-4,5-dihydro-

InChi Key

IQVQXVFMNOFTMU-FLIBITNWSA-N

InChi Code

InChI=1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h5,7-8H,2-4,6H2,1H3/b11-8-

SMILES Code

O=C1O/C(C2=C1C=CCC2)=C\CCC

Appearance

Liquid

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ligustilide is a bioactive phthalide derivative isolated from Angelica sinensis and Chuanxiong. Ligustilide exhibits neuroprotective, anti-cancer, anti-inflammatory, and vasodilator effects.

In vitro activity:

In the investigation, ligustilide had a selective pro-apoptotic effect on prostate-CAFs. After ligustilide treatment, the proportion of CAFs in the G2-M phase of the cell cycle increased, and the expression of apoptosis-related proteins (p-P53, Bcl-2, Caspase9 and Cytochrome C) changed. Ligustilide blocks the CAF cell cycle and induces the apoptosis of CAFs. Reference: Food Chem Toxicol. 2020 Jan;135:110991. https://pubmed.ncbi.nlm.nih.gov/31765699/

In vivo activity:

This study found that ligustilide (Lig), a novel Smad3 covalent inhibitor, effectively inhibited airway remodeling in cigarette smoke (CS) combined with lipopolysaccharide (LPS)-induced COPD mice. These findings provide experimental support that Lig attenuates COPD by repressing airway remodeling which is attributed to its suppression on the activation of EMT process in the airway epithelium via targeting Smad3 and inhibiting the recruitment of the Smad3-SARA heterodimer in the TGF-β1/Smad3 pathway. Reference: Phytother Res. 2022 Oct 10. https://pubmed.ncbi.nlm.nih.gov/36216328/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	100.0	525.65

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 190.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Ma J, Mei J, Lu J, Wang Y, Hu M, Ma F, Long H, Qin Z, Tao N. Ligustilide promotes apoptosis of cancer-associated fibroblasts via the TLR4 pathways. Food Chem Toxicol. 2020 Jan;135:110991. doi: 10.1016/j.fct.2019.110991. Epub 2019 Nov 22. PMID: 31765699. 2. Choi ES, Yoon JJ, Han BH, Jeong DH, Lee YJ, Kang DG, Lee HS. Ligustilide attenuates vascular inflammation and activates Nrf2/HO-1 induction and, NO synthesis in HUVECs. Phytomedicine. 2018 Jan 1;38:12-23. doi: 10.1016/j.phymed.2017.09.022. Epub 2017 Oct 4. PMID: 29425644. 3. Lu YJ, Niu L, Shen FK, Yang W, Xie Y, Li SY, Jiang M, Bai G. Ligustilide attenuates airway remodeling in COPD mice by covalently binding to MH2 domain of Smad3 in pulmonary epithelium, disrupting the Smad3-SARA interaction. Phytother Res. 2022 Oct 10. doi: 10.1002/ptr.7655. Epub ahead of print. PMID: 36216328. 4. Peng D, Wang YX, Huang TH, Luo D, Qiao LJ, Wang Q, Guan L, Cai YF, Zhang SJ. Ligustilide Improves Cognitive Impairment via Regulating the SIRT1/IRE1α/XBP1s/CHOP Pathway in Vascular Dementia Rats. Oxid Med Cell Longev. 2022 Aug 16;2022:6664990. doi: 10.1155/2022/6664990. PMID: 36017237; PMCID: PMC9398841.

In vitro protocol:

In vivo protocol:

1. Lu YJ, Niu L, Shen FK, Yang W, Xie Y, Li SY, Jiang M, Bai G. Ligustilide attenuates airway remodeling in COPD mice by covalently binding to MH2 domain of Smad3 in pulmonary epithelium, disrupting the Smad3-SARA interaction. Phytother Res. 2022 Oct 10. doi: 10.1002/ptr.7655. Epub ahead of print. PMID: 36216328. 2. Peng D, Wang YX, Huang TH, Luo D, Qiao LJ, Wang Q, Guan L, Cai YF, Zhang SJ. Ligustilide Improves Cognitive Impairment via Regulating the SIRT1/IRE1α/XBP1s/CHOP Pathway in Vascular Dementia Rats. Oxid Med Cell Longev. 2022 Aug 16;2022:6664990. doi: 10.1155/2022/6664990. PMID: 36017237; PMCID: PMC9398841.

1: Shi Y, Wang D, Lu L, Yin Y, Wang M, Li C, Diao J, Wang Y, Wei L. Ligustilide prevents the apoptosis effects of tumour necrosis factor-alpha during C2C12 cell differentiation. Int Immunopharmacol. 2014 Apr;19(2):358-64. doi: 10.1016/j.intimp.2014.02.007. Epub 2014 Feb 21. PubMed PMID: 24560902. 2: Wu Z, Uchi H, Morino-Koga S, Nakamura-Satomura A, Kita K, Shi W, Furue M. Z-Ligustilide inhibits benzo(a)pyrene-induced CYP1A1 upregulation in cultured human keratinocytes via ROS-dependent Nrf2 activation. Exp Dermatol. 2014 Apr;23(4):260-5. doi: 10.1111/exd.12360. PubMed PMID: 24588654. 3: Zuo AH, Wang L, Xiao HB. [Research progress studies on pharmacology and pharmacokinetics of ligustilide]. Zhongguo Zhong Yao Za Zhi. 2012 Nov;37(22):3350-3. Review. Chinese. PubMed PMID: 23373200. 4: Yu J, Jiang Z, Ning L, Zhao Z, Yang N, Chen L, Ma H, Li L, Fu Y, Zhu H, Qi H. Protective HSP70 Induction by Z-Ligustilide against Oxygen-Glucose Deprivation Injury via Activation of the MAPK Pathway but Not of HSF1. Biol Pharm Bull. 2015;38(10):1564-72. doi: 10.1248/bpb.b15-00352. Epub 2015 Jul 22. PubMed PMID: 26212861. 5: Zhu MD, Zhao LX, Wang XT, Gao YJ, Zhang ZJ. Ligustilide inhibits microglia-mediated proinflammatory cytokines production and inflammatory pain. Brain Res Bull. 2014 Oct;109:54-60. doi: 10.1016/j.brainresbull.2014.10.002. Epub 2014 Oct 16. PubMed PMID: 25305342. 6: Zeng Q, Jia YW, Xu PL, Xiao MW, Liu YM, Peng SL, Liao X. Quick and selective extraction of Z-ligustilide from Angelica sinensis using magnetic multiwalled carbon nanotubes. J Sep Sci. 2015 Dec;38(24):4269-75. doi: 10.1002/jssc.201500862. Epub 2015 Nov 19. PubMed PMID: 26496363. 7: Zhang MX, Yu Y, Du JR. [Protective effects of Z-ligustilide against cytotoxicity induced by Abeta25-35 in neuron cells]. Sichuan Da Xue Xue Bao Yi Xue Ban. 2012 Jan;43(1):34-7. Chinese. PubMed PMID: 22455127. 8: Shi Y, Xiao L, Yin Y, Wei L. Ligustilide inhibits tumour necrosis factor-alpha-induced autophagy during C2C12 cells differentiation. Biomed Pharmacother. 2015 Feb;69:42-6. doi: 10.1016/j.biopha.2014.11.002. Epub 2014 Nov 13. PubMed PMID: 25661336. 9: Xiao W, Yu A, Liu D, Shen J, Xu Z. Ligustilide treatment promotes functional recovery in a rat model of spinal cord injury via preventing ROS production. Int J Clin Exp Pathol. 2015 Oct 1;8(10):12005-13. eCollection 2015. PubMed PMID: 26722386; PubMed Central PMCID: PMC4680331. 10: Zhang XY, Qiao H, Shi YB. HPLC method with fluorescence detection for the determination of ligustilide in rat plasma and its pharmacokinetics. Pharm Biol. 2014 Jan;52(1):21-30. doi: 10.3109/13880209.2013.805790. Epub 2013 Sep 18. PubMed PMID: 24044763. 11: Zuo AH, Cheng MC, Zhuo RJ, Wang L, Xiao HB. Structure elucidation of degradation products of Z-ligustilide by UPLC-QTOF-MS and NMR spectroscopy. Yao Xue Xue Bao. 2013 Jun;48(6):911-6. PubMed PMID: 23984528. 12: Zeng M, Zhang J, Yang Y, Jin Y, Xiao W, Wang Z, Ding G, Yan R. An automated dual-gradient liquid chromatography-MS/MS method for the simultaneous determination of ferulic acid, ligustrazine and ligustilide in rat plasma and its application to a pharmacokinetic study. J Pharm Biomed Anal. 2014 Jan;88:354-63. doi: 10.1016/j.jpba.2013.08.038. Epub 2013 Sep 1. PubMed PMID: 24140450. 13: Qi H, Zhao J, Han Y, Lau AS, Rong J. Z-ligustilide potentiates the cytotoxicity of dopamine in rat dopaminergic PC12 cells. Neurotox Res. 2012 Nov;22(4):345-54. Epub 2012 Mar 27. PubMed PMID: 22451226. 14: Shao M, Qu K, Liu K, Zhang Y, Zhang L, Lian Z, Chen T, Liu J, Wu A, Tang Y, Zhu H. Effects of ligustilide on lipopolysaccharide-induced endotoxic shock in rabbits. Planta Med. 2011 May;77(8):809-16. doi: 10.1055/s-0030-1250573. Epub 2010 Nov 23. PubMed PMID: 21104607. 15: Chung JW, Choi RJ, Seo EK, Nam JW, Dong MS, Shin EM, Guo LY, Kim YS. Anti-inflammatory effects of (Z)-ligustilide through suppression of mitogen-activated protein kinases and nuclear factor-κB activation pathways. Arch Pharm Res. 2012 Mar;35(4):723-32. doi: 10.1007/s12272-012-0417-z. Epub 2012 May 3. PubMed PMID: 22553066. 16: Du H, Zhou N, Li J, Fan F. [A cell membrane chromatography method for investigation of 5-hydroxytryptamine receptor-ligustilide interaction]. Se Pu. 2015 May;33(5):530-4. Chinese. PubMed PMID: 26387212. 17: Ding C, Sheng Y, Zhang Y, Zhang J, Du G. Identification and comparison of metabolites after oral administration of essential oil of Ligusticum chuanxiong or its major constituent ligustilide in rats. Planta Med. 2008 Nov;74(14):1684-92. doi: 10.1055/s-0028-1088309. Epub 2008 Oct 24. PubMed PMID: 18951338. 18: Kuang X, Chen YS, Wang LF, Li YJ, Liu K, Zhang MX, Li LJ, Chen C, He Q, Wang Y, Du JR. Klotho upregulation contributes to the neuroprotection of ligustilide in an Alzheimer's disease mouse model. Neurobiol Aging. 2014 Jan;35(1):169-78. doi: 10.1016/j.neurobiolaging.2013.07.019. Epub 2013 Aug 21. PubMed PMID: 23973442. 19: Gao Y, Chen R, Gu N, He XL, Yang ZJ, Zuo KK. [Effects of ligustilide on the extracellular recombinant human heat shock protein 60 induced inflammatory reactions in the THP-1 cells and the related mechanisms]. Zhonghua Xin Xue Guan Bing Za Zhi. 2016 Sep 24;44(9):793-798. doi: 10.3760/cma.j.issn.0253-3758.2016.09.012. Chinese. PubMed PMID: 27667279. 20: Qi H, Han Y, Rong J. Potential roles of PI3K/Akt and Nrf2-Keap1 pathways in regulating hormesis of Z-ligustilide in PC12 cells against oxygen and glucose deprivation. Neuropharmacology. 2012 Mar;62(4):1659-70. doi: 10.1016/j.neuropharm.2011.11.012. Epub 2011 Nov 29. PubMed PMID: 22146407.