Mimosine | CAS#76177-28-1 | HIF inducer

MedKoo Cat#: 584733 | Name: Mimosine

Description:

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

Mimosine, a plant amino acid, is known to act as a normoxic inducer of hypoxia-inducible factor (HIF).

Chemical Structure

Mimosine

CAS#76177-28-1

Theoretical Analysis

MedKoo Cat#: 584733

Name: Mimosine

CAS#: 76177-28-1

Chemical Formula: C15H14N2O5

Exact Mass: 302.0903

Molecular Weight: 302.29

Elemental Analysis: C, 59.60; H, 4.67; N, 9.27; O, 26.46

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Mimocine; Mimosine

IUPAC/Chemical Name

Propanamide, N-((5,8-dihydro-7-methoxy-6-methyl-5,8-dioxo-1-isoquinolinyl)methyl)-2-oxo-

InChi Key

IYYSRVPPIJVVJO-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H14N2O5/c1-7-12(19)9-4-5-16-10(6-17-15(21)8(2)18)11(9)13(20)14(7)22-3/h4-5H,6H2,1-3H3,(H,17,21)

SMILES Code

CC(C(NCC1=NC=CC(C(C(C)=C2OC)=O)=C1C2=O)=O)=O

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

Preparing Stock Solutions

The following data is based on the product molecular weight 302.29 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

1: Nguyen BC, Tawata S. The Chemistry and Biological Activities of Mimosine: A Review. Phytother Res. 2016 Aug;30(8):1230-42. doi: 10.1002/ptr.5636. Epub 2016 May 23. Review. PubMed PMID: 27213712. 2: Nguyen BC, Tawata S. Mimosine Dipeptide Enantiomsers: Improved Inhibitors against Melanogenesis and Cyclooxygenase. Molecules. 2015 Aug 6;20(8):14334-47. doi: 10.3390/molecules200814334. PubMed PMID: 26287130. 3: Kuroyanagi G, Otsuka T, Yamamoto N, Kainuma S, Ohguchi R, Fujita K, Matsushima-Nishiwaki R, Kozawa O, Tokuda H. Mimosine suppresses the PGF2α-induced synthesis of osteoprotegerin but not interleukin-6 in osteoblasts. Int J Mol Med. 2016 Feb;37(2):533-41. doi: 10.3892/ijmm.2016.2452. Epub 2016 Jan 7. PubMed PMID: 26744072. 4: Li XW, Hu CP, Li YJ, Gao YX, Wang XM, Yang JR. Inhibitory effect of l-mimosine on bleomycin-induced pulmonary fibrosis in rats: Role of eIF3a and p27. Int Immunopharmacol. 2015 Jul;27(1):53-64. doi: 10.1016/j.intimp.2015.04.048. Epub 2015 May 5. PubMed PMID: 25957199. 5: Nguyen BC, Chompoo J, Tawata S. Insecticidal and Nematicidal Activities of Novel Mimosine Derivatives. Molecules. 2015 Sep 14;20(9):16741-56. doi: 10.3390/molecules200916741. PubMed PMID: 26389870. 6: Derakhshani H, Corley SW, Al Jassim R. Isolation and characterization of mimosine, 3, 4 DHP and 2, 3 DHP degrading bacteria from a commercial rumen inoculum. J Basic Microbiol. 2016 May;56(5):580-5. doi: 10.1002/jobm.201500590. Epub 2016 Jan 15. PubMed PMID: 26773324. 7: Crawford G, Puschner B, Affolter V, Stalis I, Davidson A, Baker T, Tahara J, Jolly A, Ostapak S. Systemic effects of Leucaena leucocephala ingestion on ringtailed lemurs (Lemur catta) at Berenty Reserve, Madagascar. Am J Primatol. 2015 Jun;77(6):633-41. doi: 10.1002/ajp.22386. Epub 2015 Mar 21. PubMed PMID: 25809223. 8: Janjić K, Edelmayer M, Moritz A, Agis H. L-mimosine and hypoxia can increase angiogenin production in dental pulp-derived cells. BMC Oral Health. 2017 May 25;17(1):87. doi: 10.1186/s12903-017-0373-6. PubMed PMID: 28545523; PubMed Central PMCID: PMC5445368. 9: Kuroyanagi G, Tokuda H, Yamamoto N, Kainuma S, Fujita K, Ohguchi R, Matsushima-Nishiwaki R, Kozawa O, Otsuka T. Attenuation of prostaglandin E1 induced osteoprotegerin synthesis in osteoblasts by normoxic HIF inducers. Mol Med Rep. 2017 Apr;15(4):1847-1852. doi: 10.3892/mmr.2017.6177. Epub 2017 Feb 8. PubMed PMID: 28259984. 10: Negi VS, Bingham JP, Li QX, Borthakur D. A carbon-nitrogen lyase from Leucaena leucocephala catalyzes the first step of mimosine degradation. Plant Physiol. 2014 Feb;164(2):922-34. doi: 10.1104/pp.113.230870. Epub 2013 Dec 18. PubMed PMID: 24351687; PubMed Central PMCID: PMC3912116. 11: Soltan YA, Morsy AS, Sallam SM, Lucas RC, Louvandini H, Kreuzer M, Abdalla AL. Contribution of condensed tannins and mimosine to the methane mitigation caused by feeding Leucaena leucocephala. Arch Anim Nutr. 2013 Jun;67(3):169-84. doi: 10.1080/1745039X.2013.801139. PubMed PMID: 23742642. 12: Ogita S, Kato M, Watanabe S, Ashihara H. The co-occurrence of two pyridine alkaloids, mimosine and trigonelline, in Leucaena leucocephala. Z Naturforsch C. 2014 Mar-Apr;69(3-4):124-32. PubMed PMID: 24873033. 13: Fallon AM. Effects of mimosine on Wolbachia in mosquito cells: cell cycle suppression reduces bacterial abundance. In Vitro Cell Dev Biol Anim. 2015 Oct;51(9):958-63. doi: 10.1007/s11626-015-9918-7. Epub 2015 May 28. PubMed PMID: 26019119; PubMed Central PMCID: PMC4982391. 14: Janjić K, Alhujazy U, Moritz A, Agis H. L-mimosine and hypoxia enhance angiopoietin-like 4 production involving hypoxia-inducible factor-1alpha: Insights from monolayer and spheroid cultures of dental pulp-derived cells and tooth slice cultures. Arch Oral Biol. 2018 Jan;85:172-177. doi: 10.1016/j.archoralbio.2017.10.011. Epub 2017 Oct 16. PubMed PMID: 29100106. 15: Fang Y, Zhang H, Zhong Y, Ding X. Prolyl hydroxylase 2 (PHD2) inhibition protects human renal epithelial cells and mice kidney from hypoxia injury. Oncotarget. 2016 Aug 23;7(34):54317-54328. doi: 10.18632/oncotarget.11104. PubMed PMID: 27527871; PubMed Central PMCID: PMC5342344. 16: Rashid MH, Iwasaki H, Oogai S, Fukuta M, Parveen S, Hossain MA, Anai T, Oku H. Molecular characterization of cytosolic cysteine synthase in Mimosa pudica. J Plant Res. 2018 Mar;131(2):319-329. doi: 10.1007/s10265-017-0986-5. Epub 2017 Nov 27. PubMed PMID: 29181648. 17: Negi VS, Borthakur D. Heterologous Expression and Characterization of Mimosinase from Leucaena leucocephala. Methods Mol Biol. 2016;1405:59-77. doi: 10.1007/978-1-4939-3393-8_7. PubMed PMID: 26843166. 18: Nokihara K, Hirata A, Sogon T, Ohyama T. Preparative scale isolation, purification and derivatization of mimosine, a non-proteinogenic amino acid. Amino Acids. 2012 Jul;43(1):475-82. doi: 10.1007/s00726-011-1104-y. Epub 2011 Oct 13. PubMed PMID: 21993536. 19: Trimmel K, Cvikl B, Müller HD, Nürnberger S, Gruber R, Moritz A, Agis H. L-mimosine increases the production of vascular endothelial growth factor in human tooth slice organ culture model. Int Endod J. 2015 Mar;48(3):252-60. doi: 10.1111/iej.12307. Epub 2014 Jun 28. PubMed PMID: 24786562. 20: Yafuso JT, Negi VS, Bingham JP, Borthakur D. An O-acetylserine (thiol) lyase from Leucaena leucocephala is a cysteine synthase but not a mimosine synthase. Appl Biochem Biotechnol. 2014 Jul;173(5):1157-68. doi: 10.1007/s12010-014-0917-z. Epub 2014 Apr 29. PubMed PMID: 24777760.