Butyrolactone I | CAS#87414-49-1 |

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

MedKoo CAT#: 592694

CAS#: 87414-49-1

Description: Butyrolactone I is a Selective inhibitor of cdk2 & cdc2 kinase..

Chemical Structure

Butyrolactone I

CAS# 87414-49-1

Instruction

Theoretical Analysis

MedKoo Cat#: 592694
Name: Butyrolactone I
CAS#: 87414-49-1
Chemical Formula: C24H24O7
Exact Mass: 424.15
Molecular Weight: 424.449
Elemental Analysis: C, 67.91; H, 5.70; O, 26.39

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 350	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Butyrolactone I

IUPAC/Chemical Name: 2-Furancarboxylic acid, 2,5-dihydro-4-hydroxy-2-((4-hydroxy-3-(3-methyl-2-butenyl)phenyl)methyl)-3-(4-hydroxyphenyl)-5-oxo-, methyl ester

InChi Key: NGOLMNWQNHWEKU-UHFFFAOYSA-N

InChi Code: InChI=1S/C24H24O7/c1-14(2)4-6-17-12-15(5-11-19(17)26)13-24(23(29)30-3)20(21(27)22(28)31-24)16-7-9-18(25)10-8-16/h4-5,7-12,25-27H,6,13H2,1-3H3

SMILES Code: O=C(C(C(C1=CC=C(O)C=C1)=C2O)(CC3=CC=C(O)C(C/C=C(C)\C)=C3)OC2=O)OC

Appearance: Solid powder

Purity: >98% (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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 424.45 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:
In vitro protocol:
In vivo protocol:

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1: Palonen EK, Neffling MR, Raina S, Brandt A, Keshavarz T, Meriluoto J, Soini J. Butyrolactone I Quantification from Lovastatin Producing Aspergillus terreus Using Tandem Mass Spectrometry-Evidence of Signalling Functions. Microorganisms. 2014 Jun 4;2(2):111-27. doi: 10.3390/microorganisms2020111. PubMed PMID: 27682234; PubMed Central PMCID: PMC5029482.

2: Maziero RR, Guaitolini CR, Paschoal DM, Kievitsbosch T, Guastali MD, Moraes CN, Landim-Alvarenga FC. Effect of Temporary Meiotic Attenuation of Oocytes with Butyrolactone I and Roscovitine in Resistance to Bovine Embryos on Vitrification. Reprod Domest Anim. 2016 Apr;51(2):204-11. doi: 10.1111/rda.12667. Epub 2016 Jan 27. PubMed PMID: 26812982.

3: Kitagawa M, Higashi H, Takahashi IS, Okabe T, Ogino H, Taya Y, Hishimura S, Okuyama A. A cyclin-dependent kinase inhibitor, butyrolactone I, inhibits phosphorylation of RB protein and cell cycle progression. Oncogene. 1994 Sep;9(9):2549-57. PubMed PMID: 8058318.

4: Grupen CG, Fung M, Armstrong DT. Effects of milrinone and butyrolactone-I on porcine oocyte meiotic progression and developmental competence. Reprod Fertil Dev. 2006;18(3):309-17. PubMed PMID: 16554006.

5: Niu X, Dahse HM, Menzel KD, Lozach O, Walther G, Meijer L, Grabley S, Sattler I. Butyrolactone I derivatives from Aspergillus terreus carrying an unusual sulfate moiety. J Nat Prod. 2008 Apr;71(4):689-92. doi: 10.1021/np070341r. Epub 2008 Feb 14. PubMed PMID: 18271552.

6: Wu GM, Sun QY, Mao J, Lai L, McCauley TC, Park KW, Prather RS, Didion BA, Day BN. High developmental competence of pig oocytes after meiotic inhibition with a specific M-phase promoting factor kinase inhibitor, butyrolactone I. Biol Reprod. 2002 Jul;67(1):170-7. PubMed PMID: 12080014.

7: Nishio K, Ishida T, Arioka H, Kurokawa H, Fukuoka K, Nomoto T, Fukumoto H, Yokote H, Saijo N. Antitumor effects of butyrolactone I, a selective cdc2 kinase inhibitor, on human lung cancer cell lines. Anticancer Res. 1996 Nov-Dec;16(6B):3387-95. PubMed PMID: 9042196.

8: Leal CL, Mamo S, Fair T, Lonergan P. Gene expression in bovine oocytes and cumulus cells after meiotic inhibition with the cyclin-dependent kinase inhibitor butyrolactone I. Reprod Domest Anim. 2012 Aug;47(4):615-24. doi: 10.1111/j.1439-0531.2011.01932.x. Epub 2011 Oct 28. PubMed PMID: 22034924.

9: Hida D, Nakata K, Shima Y, Migita K, Nakao K, Kato Y, Ishii N, Eguchi K. Suppression of albumin and alpha-fetoprotein gene expression by butyrolactone I, a selective inhibitor of the cdk family, in HuH-7 human hepatoma cells. Anticancer Res. 1998 Nov-Dec;18(6A):4317-22. PubMed PMID: 9891485.

10: Schimmel TG, Coffman AD, Parsons SJ. Effect of butyrolactone I on the producing fungus, Aspergillus terreus. Appl Environ Microbiol. 1998 Oct;64(10):3707-12. PubMed PMID: 9758788; PubMed Central PMCID: PMC106526.

11: Kitagawa M, Okabe T, Ogino H, Matsumoto H, Suzuki-Takahashi I, Kokubo T, Higashi H, Saitoh S, Taya Y, Yasuda H, et al. Butyrolactone I, a selective inhibitor of cdk2 and cdc2 kinase. Oncogene. 1993 Sep;8(9):2425-32. PubMed PMID: 8395680.

12: An X, Feng BM, Chen G, Chen SF, Bai J, Hua HM, Wang HF, Pei YH. Isolation and identification of phase I metabolites of butyrolactone I in rats. Xenobiotica. 2017 Mar;47(3):236-244. doi: 10.3109/00498254.2016.1172280. Epub 2016 Sep 8. PubMed PMID: 27604497.

13: Someya A, Tanaka N, Okuyama A. Inhibition of cell cycle oscillation of DNA replication by a selective inhibitor of the cdc2 kinase family, butyrolactone I, in Xenopus egg extracts. Biochem Biophys Res Commun. 1994 Jan 28;198(2):536-45. PubMed PMID: 8297363.

14: Braña MF, García ML, López B, de Pascual-Teresa B, Ramos A, Pozuelo JM, Domínguez MT. Synthesis and biological evaluation of analogues of butyrolactone I and molecular model of its interaction with CDK2. Org Biomol Chem. 2004 Jul 7;2(13):1864-71. Epub 2004 Jun 16. PubMed PMID: 15227538.

15: Ferreira EM, Vireque AA, Adona PR, Ferriani RA, Navarro PA. Prematuration of bovine oocytes with butyrolactone I reversibly arrests meiosis without increasing meiotic abnormalities after in vitro maturation. Eur J Obstet Gynecol Reprod Biol. 2009 Jul;145(1):76-80. doi: 10.1016/j.ejogrb.2009.03.016. Epub 2009 Apr 28. PubMed PMID: 19403233.

16: Wada M, Hosotani R, Lee JU, Doi R, Koshiba T, Fujimoto K, Miyamoto Y, Tsuji S, Nakajima S, Okuyama A, Imamura M. An exogenous cdk inhibitor, butyrolactone-I, induces apoptosis with increased Bax/Bcl-2 ratio in p53-mutated pancreatic cancer cells. Anticancer Res. 1998 Jul-Aug;18(4A):2559-66. PubMed PMID: 9703910.

17: Hirao Y, Nishimoto N, Kure-bayashi S, Takenouchi N, Yamauchi N, Masuda H, Nagai T. Influence of meiotic inhibition by butyrolactone-I during germinal vesicle stage on the ability of porcine oocytes to be activated by electric stimulation after nuclear maturation. Zygote. 2003 Aug;11(3):191-7. PubMed PMID: 14640183.

18: Adona PR, Pires PR, Quetglas MD, Schwarz KR, Leal CL. Prematuration of bovine oocytes with butyrolactone I: effects on meiosis progression, cytoskeleton, organelle distribution and embryo development. Anim Reprod Sci. 2008 Oct;108(1-2):49-65. Epub 2007 Jul 13. PubMed PMID: 17692479.

19: Lonergan P, Dinnyes A, Fair T, Yang X, Boland M. Bovine oocyte and embryo development following meiotic inhibition with butyrolactone I. Mol Reprod Dev. 2000 Oct;57(2):204-9. PubMed PMID: 10984421.

20: Suzuki M, Hosaka Y, Matsushima H, Goto T, Kitamura T, Kawabe K. Butyrolactone I induces cyclin B1 and causes G2/M arrest and skipping of mitosis in human prostate cell lines. Cancer Lett. 1999 Apr 26;138(1-2):121-30. PubMed PMID: 10378783.

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Butyrolactone I featured