MedKoo Cat#: 597980 | Name: Porphyra 334

Description:

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

Porphyra 334 is a mycosporine-like amino acid. Porphyra 334 is an analogue of Shinorine. Porphyra-334 and shinorine are antioxidants and direct antagonists of Keap1-Nrf2 binding. Porphyra 334 may be a useful agent to prevent or retard the progression of multiple degenerative disorders of ageing. Porphyra-334 inhibits UV-induced apoptosis in HaCaT cells through attenuation of the caspase pathway. The structure of Porphyra 334 is very sunular to that of Shinorine. The latter is a demethyl-analog of Porphyra 334.

Chemical Structure

Porphyra 334
Porphyra 334
CAS#70579-26-9

Theoretical Analysis

MedKoo Cat#: 597980

Name: Porphyra 334

CAS#: 70579-26-9

Chemical Formula: C14H22N2O8

Exact Mass: 346.1376

Molecular Weight: 346.33

Elemental Analysis: C, 48.55; H, 6.40; N, 8.09; O, 36.96

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
Porphyra 334; Porphyra-334; Porphyra334; mytilin B;
IUPAC/Chemical Name
(2S,3R)-2-(((S,E)-3-((carboxymethyl)amino)-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene)amino)-3-hydroxybutanoic acid
InChi Key
VIZAVBQHHMQOQF-FCDTZTNESA-N
InChi Code
InChI=1S/C14H22N2O8/c1-7(18)11(13(21)22)16-9-4-14(23,6-17)3-8(12(9)24-2)15-5-10(19)20/h7,11,15,17-18,23H,3-6H2,1-2H3,(H,19,20)(H,21,22)/b16-9+/t7-,11+,14+/m1/s1
SMILES Code
C[C@@H](O)[C@H](/N=C1C[C@@](CO)(O)CC(NCC(O)=O)=C\1OC)C(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
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 346.33 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: Kim SY, Cho WK, Kim HI, Paek SH, Jang SJ, Jo Y, Choi H, Lee JH, Moh SH. Transcriptome Profiling of Human Follicle Dermal Papilla Cells in response to Porphyra-334 Treatment by RNA-Seq. Evid Based Complement Alternat Med. 2021 Jan 13;2021:6637513. doi: 10.1155/2021/6637513. PMID: 33519944; PMCID: PMC7817261. 2: Yoo J, Kim J, Lee JH, Kim H, Jang SJ, Seo HH, Oh ST, Hyeon SJ, Ryu H, Kim J, Moh SH. Acceleration of somatic cell reprogramming into the induced pluripotent stem cell using a mycosporine-like amino acid, Porphyra 334. Sci Rep. 2020 Feb 28;10(1):3684. doi: 10.1038/s41598-020-60680-5. PMID: 32111890; PMCID: PMC7048830. 3: Hatakeyama M, Koizumi K, Boero M, Nobusada K, Hori H, Misonou T, Kobayashi T, Nakamura S. Unique Structural Relaxations and Molecular Conformations of Porphyra-334 at the Excited State. J Phys Chem B. 2019 Sep 12;123(36):7649-7656. doi: 10.1021/acs.jpcb.9b03744. Epub 2019 Aug 29. PMID: 31430154. 4: 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. 5: Suh SS, Lee SG, Youn UJ, Han SJ, Kim IC, Kim S. Comprehensive Expression Profiling and Functional Network Analysis of Porphyra-334, One Mycosporine-Like Amino Acid (MAA), in Human Keratinocyte Exposed with UV-radiation. Mar Drugs. 2017 Jun 24;15(7):196. doi: 10.3390/md15070196. PMID: 28672785; PMCID: PMC5532638. 6: Suh SS, Oh SK, Lee SG, Kim IC, Kim S. Porphyra-334, a mycosporine-like amino acid, attenuates UV-induced apoptosis in HaCaT cells. Acta Pharm. 2017 Jun 27;67(2):257-264. doi: 10.1515/acph-2017-0015. PMID: 28590914. 7: Ishihara K, Watanabe R, Uchida H, Suzuki T, Yamashita M, Takenaka H, Nazifi E, Matsugo S, Yamaba M, Sakamoto T. Novel glycosylated mycosporine-like amino acid, 13-O-(β-galactosyl)-porphyra-334, from the edible cyanobacterium Nostoc sphaericum-protective activity on human keratinocytes from UV light. J Photochem Photobiol B. 2017 Jul;172:102-108. doi: 10.1016/j.jphotobiol.2017.05.019. Epub 2017 May 15. PMID: 28544967. 8: 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. 9: Ryu J, Kwon MJ, Nam TJ. Nrf2 and NF-κB Signaling Pathways Contribute to Porphyra-334-Mediated Inhibition of UVA-Induced Inflammation in Skin Fibroblasts. Mar Drugs. 2015 Jul 31;13(8):4721-32. doi: 10.3390/md13084721. PMID: 26264001; PMCID: PMC4557001. 10: Chuang LF, Chou HN, Sung PJ. Porphyra-334 isolated from the marine algae Bangia atropurpurea: conformational performance for energy conversion. Mar Drugs. 2014 Sep 3;12(9):4732-40. doi: 10.3390/md12094732. PMID: 25192413; PMCID: PMC4178487. 11: Ryu J, Park SJ, Kim IH, Choi YH, Nam TJ. Protective effect of porphyra-334 on UVA-induced photoaging in human skin fibroblasts. Int J Mol Med. 2014 Sep;34(3):796-803. doi: 10.3892/ijmm.2014.1815. Epub 2014 Jun 19. PMID: 24946848; PMCID: PMC4121349. 12: Nazifi E, Wada N, Yamaba M, Asano T, Nishiuchi T, Matsugo S, Sakamoto T. Glycosylated porphyra-334 and palythine-threonine from the terrestrial cyanobacterium Nostoc commune. Mar Drugs. 2013 Aug 26;11(9):3124-54. doi: 10.3390/md11093124. PMID: 24065157; PMCID: PMC3801118. 13: Bhatia S, Sharma K, Namdeo AG, Chaugule BB, Kavale M, Nanda S. Broad- spectrum sun-protective action of Porphyra-334 derived from Porphyra vietnamensis. Pharmacognosy Res. 2010 Jan;2(1):45-9. doi: 10.4103/0974-8490.60578. PMID: 21808539; PMCID: PMC3140129. 14: Torres A, Enk CD, Hochberg M, Srebnik M. Porphyra-334, a potential natural source for UVA protective sunscreens. Photochem Photobiol Sci. 2006 Apr;5(4):432-5. doi: 10.1039/b517330m. Epub 2006 Feb 17. PMID: 16583025. 15: 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. 16: Conde FR, Churio MS, Previtali CM. The photoprotector mechanism of mycosporine-like amino acids. Excited-state properties and photostability of porphyra-334 in aqueous solution. J Photochem Photobiol B. 2000 Jul;56(2-3):139-44. doi: 10.1016/s1011-1344(00)00066-x. PMID: 11079474.