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

MedKoo CAT#: 561411

CAS#: 551-08-6

Description: Butylidenephthalide is an inhibitor of platelet-derived growth factor (PDGF). Butylidenephthalide activity leads to the reduction of liver fibrosis, increased Nur77 (NR4A1) expression, and downregulation of EMT-related genes such as Snail (Snail/SNAI1) and Slug (Slug/SNAI2)


Chemical Structure

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Butylidenephthalide
CAS# 551-08-6

Theoretical Analysis

MedKoo Cat#: 561411
Name: Butylidenephthalide
CAS#: 551-08-6
Chemical Formula: C12H12O2
Exact Mass: 188.08
Molecular Weight: 188.230
Elemental Analysis: C, 76.57; H, 6.43; O, 17.00

Price and Availability

Size Price Availability Quantity
10g USD 250 2 Weeks
50g USD 450 2 Weeks
250g USD 1050 2 Weeks
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Synonym: Butylidenephthalide; BP; 3-Butylidene Phthalide

IUPAC/Chemical Name: 3-Butylidene-2-benzofuran-1-one

InChi Key: WMBOCUXXNSOQHM-FLIBITNWSA-N

InChi Code: InChI=1S/C12H12O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-8H,2-3H2,1H3/b11-8-

SMILES Code: O=C(C1=CC=CC=C1/2)OC2=C/CCC

Appearance: Solid powder

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: >2 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: 2934.99.9001

More Info:

Product Data:
Biological target: 3-Butylidenephthalide (Butylidenephthalide) is a phthalic anhydride derivative identified in Ligusticum chuanxiong Hort, and has larvicidal activity (LC50 of 1.56 mg/g for Spodoptera litura larvae).
In vitro activity: To establish an in vitro model that could mimic the responses of n-BP (n-butylidenephthalide) in SCA3 cerebellum, both HEK-293 cells expressing either GFP-ATXN3-28Q (control) or 84Q were used (Figure 3F). Reduced protein level of the GFP-ATXN3-84Q (m-ATXN3 and TFs) was observed, and this could have been the consequence of autophagy promotion by n-BP treatment. Both cellular and murine LC3B-II or p62 to GAPDH ratios were quantified using ImageJ software (Figure 3E,G), and the findings showed that n-BP could enhance autophagy. Reference: Int J Mol Sci. 2021 Jun; 22(12): 6339. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8231882/
In vivo activity: Human ovarian cancer xenografts were used to investigate the tumor-inhibiting effect of BP (butylidenephthalide) in mice. With BP treatment (200 mg/kg) in KURAMOCHI and OVSAHO cells, the tumor volumes were smaller than those of control mice treated with the vehicle (days 11-26 in KURAMOCHI [p < 0.001], day 14 -21 in OVSAHO [P<0.05]) (Fig. 8A, 9A). Reference: J Cancer. 2021; 12(11): 3126–3135. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8100814/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 250.0 1,328.16

Preparing Stock Solutions

The following data is based on the product molecular weight 188.23 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.

Recalculate based on batch purity %
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. Lee JH, Lin SY, Liu JW, Lin SZ, Harn HJ, Chiou TW. n-Butylidenephthalide Modulates Autophagy to Ameliorate Neuropathological Progress of Spinocerebellar Ataxia Type 3 through mTOR Pathway. Int J Mol Sci. 2021 Jun 13;22(12):6339. doi: 10.3390/ijms22126339. PMID: 34199295; PMCID: PMC8231882. 2. Lin YL, Huang XF, Chang KF, Liao KW, Tsai NM. Encapsulated n-Butylidenephthalide Efficiently Crosses the Blood-Brain Barrier and Suppresses Growth of Glioblastoma. Int J Nanomedicine. 2020 Jan 31;15:749-760. doi: 10.2147/IJN.S235815. PMID: 32099363; PMCID: PMC6999785. 3. Chang YH, Wu KC, Ding DC. The natural compound n-butylidenephthalide kills high-grade serous ovarian cancer stem cells by activating intrinsic apoptosis signaling pathways. J Cancer. 2021 Mar 30;12(11):3126-3135. doi: 10.7150/jca.51650. PMID: 33976722; PMCID: PMC8100814. 4. Yang HH, Xu YX, Chen JY, Harn HJ, Chiou TW. N-Butylidenephthalide Inhibits the Phenotypic Switch of VSMCs through Activation of AMPK and Prevents Stenosis in an Arteriovenous Fistula Rat Model. Int J Mol Sci. 2020 Oct 7;21(19):7403. doi: 10.3390/ijms21197403. PMID: 33036484; PMCID: PMC7582375.
In vitro protocol: 1. Lee JH, Lin SY, Liu JW, Lin SZ, Harn HJ, Chiou TW. n-Butylidenephthalide Modulates Autophagy to Ameliorate Neuropathological Progress of Spinocerebellar Ataxia Type 3 through mTOR Pathway. Int J Mol Sci. 2021 Jun 13;22(12):6339. doi: 10.3390/ijms22126339. PMID: 34199295; PMCID: PMC8231882. 2. Lin YL, Huang XF, Chang KF, Liao KW, Tsai NM. Encapsulated n-Butylidenephthalide Efficiently Crosses the Blood-Brain Barrier and Suppresses Growth of Glioblastoma. Int J Nanomedicine. 2020 Jan 31;15:749-760. doi: 10.2147/IJN.S235815. PMID: 32099363; PMCID: PMC6999785.
In vivo protocol: 1. Chang YH, Wu KC, Ding DC. The natural compound n-butylidenephthalide kills high-grade serous ovarian cancer stem cells by activating intrinsic apoptosis signaling pathways. J Cancer. 2021 Mar 30;12(11):3126-3135. doi: 10.7150/jca.51650. PMID: 33976722; PMCID: PMC8100814. 2. Yang HH, Xu YX, Chen JY, Harn HJ, Chiou TW. N-Butylidenephthalide Inhibits the Phenotypic Switch of VSMCs through Activation of AMPK and Prevents Stenosis in an Arteriovenous Fistula Rat Model. Int J Mol Sci. 2020 Oct 7;21(19):7403. doi: 10.3390/ijms21197403. PMID: 33036484; PMCID: PMC7582375.

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1: Donkor PO, Chen Y, Ding L, Qiu F. Locally and traditionally used Ligusticum species - A review of their phytochemistry, pharmacology and pharmacokinetics. J Ethnopharmacol. 2016 Dec 24;194:530-548. doi: 10.1016/j.jep.2016.10.012. Epub 2016 Oct 10. Review. PubMed PMID: 27729283.

2: Wei WL, Zeng R, Gu CM, Qu Y, Huang LF. Angelica sinensis in China-A review of botanical profile, ethnopharmacology, phytochemistry and chemical analysis. J Ethnopharmacol. 2016 Aug 22;190:116-41. doi: 10.1016/j.jep.2016.05.023. Epub 2016 May 19. Review. PubMed PMID: 27211015.