Ectoine | CAS#96702-03-3 | protein misfolding inhibitor

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

MedKoo CAT#: 562207

CAS#: 96702-03-3

Description: Ectoine is an inhibitor of protein misfolding. It acts by significantly down-regulating Syp, Mapk3 and Tnfα and up-regulating Vegf in rat's hippocampus, prohibiting insulin amyloid formation in vitro.

Chemical Structure

Ectoine

CAS# 96702-03-3

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 562207
Name: Ectoine
CAS#: 96702-03-3
Chemical Formula: C6H10N2O2
Exact Mass: 142.07
Molecular Weight: 142.150
Elemental Analysis: C, 50.69; H, 7.09; N, 19.71; O, 22.51

Price and Availability

Size	Price	Availability
1g	USD 550	2 weeks
2g	USD 950	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: Ectoine;

IUPAC/Chemical Name: (6S)-2-Methyl-1,4,5,6-tetrahydropyrimidine-6-carboxylic acid

InChi Key: WQXNXVUDBPYKBA-YFKPBYRVSA-N

InChi Code: InChI=1S/C6H10N2O2/c1-4-7-3-2-5(8-4)6(9)10/h5H,2-3H2,1H3,(H,7,8)(H,9,10)/t5-/m0/s1

SMILES Code: O=C([C@@H]1CCN=C(C)N1)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: >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:

Product Data

Instruction:

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Biological target:	Ectoine serves as an osmoregulatory compatible solute, increasing the hydration of the skin surface and stabilizing lipid layers.
In vitro activity:	MTT data indicated that when compared to the untreated control cells, Ectoine pre-treated (0.5–1.5 μM) and 3 J/cm2 UVA exposed HaCaT cells were unable to show a significant decrease in cell viability (Figure 1B). Further, Ectoine pretreatment attenuated the UVA (3 J/cm2)-induced cell death in a dose-dependent manner (Figure 1B). Reference: Antioxidants (Basel). 2020 Jan; 9(1): 63. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7022695/
In vivo activity:	IL-1β, IL-6, IL-10, PGE2, and MDA are significantly elevated in the CNS and testes of x-irradiated rat groups when compared with controls. IL-1β, IL-6, IL-10, and PGE2 significantly elevated at one week than one day while MDA significantly decreased. A significant decrease in the concentration of GSH and in the GSH/GSSG ratios coupled with an opposite effect on GSSG was noted. Ectoine treatment significantly ameliorated the biochemical effects induced by whole body x-irradiation. Reference: Pharmacol Rep. 2018 Apr;70(2):304-308. https://pubmed.ncbi.nlm.nih.gov/29477038/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	PBS (pH 7.2)	10.0	70.35
	Water	139.0	977.84

Preparing Stock Solutions

The following data is based on the product molecular weight 142.15 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:	1. Hseu YC, Chen XZ, Vudhya Gowrisankar Y, Yen HR, Chuang JY, Yang HL. The Skin-Whitening Effects of Ectoine via the Suppression of α-MSH-Stimulated Melanogenesis and the Activation of Antioxidant Nrf2 Pathways in UVA-Irradiated Keratinocytes. Antioxidants (Basel). 2020 Jan 10;9(1):63. doi: 10.3390/antiox9010063. PMID: 31936771; PMCID: PMC7022695. 2. Schröter MA, Meyer S, Hahn MB, Solomun T, Sturm H, Kunte HJ. Ectoine protects DNA from damage by ionizing radiation. Sci Rep. 2017 Nov 10;7(1):15272. doi: 10.1038/s41598-017-15512-4. PMID: 29127339; PMCID: PMC5681641. 3. Refaat R, Sarhan D, Kotb M, El-Abd E, El-Bassiouni E. Post-irradiation protective effects of ectoine on brain and testicles in male mice. Pharmacol Rep. 2018 Apr;70(2):304-308. doi: 10.1016/j.pharep.2017.10.002. Epub 2017 Oct 4. PMID: 29477038.
In vitro protocol:	1. Hseu YC, Chen XZ, Vudhya Gowrisankar Y, Yen HR, Chuang JY, Yang HL. The Skin-Whitening Effects of Ectoine via the Suppression of α-MSH-Stimulated Melanogenesis and the Activation of Antioxidant Nrf2 Pathways in UVA-Irradiated Keratinocytes. Antioxidants (Basel). 2020 Jan 10;9(1):63. doi: 10.3390/antiox9010063. PMID: 31936771; PMCID: PMC7022695. 2. Schröter MA, Meyer S, Hahn MB, Solomun T, Sturm H, Kunte HJ. Ectoine protects DNA from damage by ionizing radiation. Sci Rep. 2017 Nov 10;7(1):15272. doi: 10.1038/s41598-017-15512-4. PMID: 29127339; PMCID: PMC5681641.
In vivo protocol:	1. Refaat R, Sarhan D, Kotb M, El-Abd E, El-Bassiouni E. Post-irradiation protective effects of ectoine on brain and testicles in male mice. Pharmacol Rep. 2018 Apr;70(2):304-308. doi: 10.1016/j.pharep.2017.10.002. Epub 2017 Oct 4. PMID: 29477038.

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*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

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1: Cantera S, Muñoz R, Lebrero R, López JC, Rodríguez Y, García-Encina PA. Technologies for the bioconversion of methane into more valuable products. Curr Opin Biotechnol. 2018 Jan 6;50:128-135. doi: 10.1016/j.copbio.2017.12.021. [Epub ahead of print] Review. PubMed PMID: 29316497.

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12: Reshetnikov AS, Khmelenina VN, Mustakhimov II, Trotsenko YA. Genes and enzymes of ectoine biosynthesis in halotolerant methanotrophs. Methods Enzymol. 2011;495:15-30. doi: 10.1016/B978-0-12-386905-0.00002-4. Review. PubMed PMID: 21419912.

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14: Pastor JM, Salvador M, Argandoña M, Bernal V, Reina-Bueno M, Csonka LN, Iborra JL, Vargas C, Nieto JJ, Cánovas M. Ectoines in cell stress protection: uses and biotechnological production. Biotechnol Adv. 2010 Nov-Dec;28(6):782-801. doi: 10.1016/j.biotechadv.2010.06.005. Epub 2010 Jul 1. Review. PubMed PMID: 20600783.

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16: Graf R, Anzali S, Buenger J, Pfluecker F, Driller H. The multifunctional role of ectoine as a natural cell protectant. Clin Dermatol. 2008 Jul-Aug;26(4):326-33. doi: 10.1016/j.clindermatol.2008.01.002. Review. PubMed PMID: 18691511.

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