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MedKoo Cat#: 535082 | Name: Shinorine

Description:

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

Shinorine, a mycosporine-like amino acid (MAA), is a small molecule sunscreen produced in some bacteria. Shinorine ameliorates chromium induced toxicity in zebrafish hepatocytes through the facultative activation of Nrf2-Keap1-ARE pathway. Shinorine is also an analogue of porphyra-344. Both porphyra-334 and shinorine are antioxidants and direct antagonists of Keap1-Nrf2 binding. Shinorine may be a useful agent to prevent or retard the progression of multiple degenerative disorders of ageing. Shinorine is a demethyl-analog of Porphyra 334.

Chemical Structure

Shinorine
Shinorine
CAS#73112-73-9

Theoretical Analysis

MedKoo Cat#: 535082

Name: Shinorine

CAS#: 73112-73-9

Chemical Formula: C13H20N2O8

Exact Mass: 332.1220

Molecular Weight: 332.31

Elemental Analysis: C, 46.99; H, 6.07; N, 8.43; O, 38.52

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.
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Related CAS #
73112-73-9
Synonym
Shinorine; demethyl-analog of Porphyra 334;
IUPAC/Chemical Name
N-(3-((Carboxymethyl)amino)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-2-cyclohexen-1-ylidene)-L-serine
InChi Key
WXEQFJUHQIGKNG-JKOAAWCESA-N
InChi Code
InChI=1S/C13H20N2O8/c1-23-11-7(14-4-10(18)19)2-13(22,6-17)3-8(11)15-9(5-16)12(20)21/h9,14,16-17,22H,2-6H2,1H3,(H,18,19)(H,20,21)/b15-8-/t9-,13?/m0/s1
SMILES Code
OC[C@@H](C(O)=O)/N=C1C(OC)=C(NCC(O)=O)CC(CO)(O)C\1
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
2934.99.9001
More Info
Mycosporine-like amino acids (MAAs) are secondary metabolites, produced by a large variety of microorganisms including algae, cyanobacteria, lichen and fungi. MAAs act as UV-absorbers and photo-protectants. MAAs are suggested to exert pharmaceutical relevant bioactivities in the human system.

Preparing Stock Solutions

The following data is based on the product molecular weight 332.31 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
1: Shaw P, Sen A, Mondal P, Dey Bhowmik A, Rath J, Chattopadhyay A. Shinorine ameliorates chromium induced toxicity in zebrafish hepatocytes through the facultative activation of Nrf2-Keap1-ARE pathway. Aquat Toxicol. 2020 Nov;228:105622. doi: 10.1016/j.aquatox.2020.105622. Epub 2020 Sep 9. PMID: 32947073. 2: Park SH, Lee K, Jang JW, Hahn JS. Metabolic Engineering of Saccharomyces cerevisiae for Production of Shinorine, a Sunscreen Material, from Xylose. ACS Synth Biol. 2019 Feb 15;8(2):346-357. doi: 10.1021/acssynbio.8b00388. Epub 2019 Jan 10. PMID: 30586497. 3: Gacesa R, Lawrence KP, Georgakopoulos ND, Yabe K, Dunlap WC, Barlow DJ, Wells G, Young AR, Long PF. The mycosporine-like amino acids porphyra-334 and shinorine are antioxidants and direct antagonists of Keap1-Nrf2 binding. Biochimie. 2018 Nov;154:35-44. doi: 10.1016/j.biochi.2018.07.020. Epub 2018 Jul 30. PMID: 30071261; PMCID: PMC6214812. 4: Tsuge Y, Kawaguchi H, Yamamoto S, Nishigami Y, Sota M, Ogino C, Kondo A. Metabolic engineering of Corynebacterium glutamicum for production of sunscreen shinorine. Biosci Biotechnol Biochem. 2018 Jul;82(7):1252-1259. doi: 10.1080/09168451.2018.1452602. Epub 2018 Mar 20. PMID: 29558858. 5: Orallo DE, Fangio MF, Poblet M, Carignan MO, Bernal L, Carreto JI, Bertolotti SG, Churio MS. Photochemistry and Photophysics of Shinorine Dimethyl Ester. Photochem Photobiol. 2018 Sep;94(5):829-833. doi: 10.1111/php.12884. Epub 2018 Mar 2. PMID: 29315606. 6: Yang G, Cozad MA, Holland DA, Zhang Y, Luesch H, Ding Y. Photosynthetic Production of Sunscreen Shinorine Using an Engineered Cyanobacterium. ACS Synth Biol. 2018 Feb 16;7(2):664-671. doi: 10.1021/acssynbio.7b00397. Epub 2018 Jan 19. PMID: 29304277. 7: Becker K, Hartmann A, Ganzera M, Fuchs D, Gostner JM. Immunomodulatory Effects of the Mycosporine-Like Amino Acids Shinorine and Porphyra-334. Mar Drugs. 2016 Jun 21;14(6):119. doi: 10.3390/md14060119. PMID: 27338421; PMCID: PMC4926078. 8: Matsuyama K, Matsumoto J, Yamamoto S, Nagasaki K, Inoue Y, Nishijima M, Mori T. pH-Independent Charge Resonance Mechanism for UV Protective Functions of Shinorine and Related Mycosporine-like Amino Acids. J Phys Chem A. 2015 Dec 24;119(51):12722-9. doi: 10.1021/acs.jpca.5b09988. Epub 2015 Dec 16. PMID: 26625701. 9: Singh G, Babele PK, Kumar A, Srivastava A, Sinha RP, Tyagi MB. Synthesis of ZnO nanoparticles using the cell extract of the cyanobacterium, Anabaena strain L31 and its conjugation with UV-B absorbing compound shinorine. J Photochem Photobiol B. 2014 Sep 5;138:55-62. doi: 10.1016/j.jphotobiol.2014.04.030. Epub 2014 May 21. PMID: 24911272. 10: Gao Q, Garcia-Pichel F. An ATP-grasp ligase involved in the last biosynthetic step of the iminomycosporine shinorine in Nostoc punctiforme ATCC 29133. J Bacteriol. 2011 Nov;193(21):5923-8. doi: 10.1128/JB.05730-11. Epub 2011 Sep 2. PMID: 21890703; PMCID: PMC3194895. 11: Singh SP, Klisch M, Sinha RP, Häder DP. Effects of abiotic stressors on synthesis of the mycosporine-like amino acid shinorine in the Cyanobacterium Anabaena variabilis PCC 7937. Photochem Photobiol. 2008 Nov-Dec;84(6):1500-5. doi: 10.1111/j.1751-1097.2008.00376.x. Epub 2008 Jun 13. PMID: 18557824. 12: Conde FR, Churio MS, Previtali CM. The deactivation pathways of the excited- states of the mycosporine-like amino acids shinorine and porphyra-334 in aqueous solution. Photochem Photobiol Sci. 2004 Oct;3(10):960-7. doi: 10.1039/b405782a. Epub 2004 Sep 6. PMID: 15480487. 13: Kräbs G, Watanabe M, Wiencke C. A monochromatic action spectrum for the photoinduction of the UV-absorbing mycosporine-like amino acid shinorine in the red alga Chondrus crispus. Photochem Photobiol. 2004 Jun;79(6):515-9. doi: 10.1562/2003-12-14-ra.1. PMID: 15291302.