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MedKoo Cat#: 146364 | Name: Hydroxyectoin

Description:

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

Hydroxyectoin is a naturally occurring amino acid derivative produced by extremophilic microorganisms as a compatible solute to protect against environmental stress. It stabilizes proteins, membranes, and other cellular structures by forming a protective hydration shell, enhancing resistance to heat, UV radiation, and desiccation.

Chemical Structure

Hydroxyectoin
Hydroxyectoin
CAS#165542-15-4

Theoretical Analysis

MedKoo Cat#: 146364

Name: Hydroxyectoin

CAS#: 165542-15-4

Chemical Formula: C6H10N2O3

Exact Mass: 158.0691

Molecular Weight: 158.16

Elemental Analysis: C, 45.57; H, 6.37; N, 17.71; O, 30.35

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 #
No Data
Synonym
Hydroxyectoin;
IUPAC/Chemical Name
(4S,5S)-5-hydroxy-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid
InChi Key
KIIBBJKLKFTNQO-WHFBIAKZSA-N
InChi Code
1S/C6H10N2O3/c1-3-7-2-4(9)5(8-3)6(10)11/h4-5,9H,2H2,1H3,(H,7,8)(H,10,11)/t4-,5-/m0/s1
SMILES Code
CC1=N[C@@H]([C@@H](O)CN1)C(O)=O
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 158.16 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: Liu M, Liu H, Shi M, Jiang M, Li L, Zheng Y. Microbial production of ectoine and hydroxyectoine as high-value chemicals. Microb Cell Fact. 2021 Mar 26;20(1):76. doi: 10.1186/s12934-021-01567-6. PMID: 33771157; PMCID: PMC7995798. 2: Jungmann L, Hoffmann SL, Lang C, De Agazio R, Becker J, Kohlstedt M, Wittmann C. High-efficiency production of 5-hydroxyectoine using metabolically engineered Corynebacterium glutamicum. Microb Cell Fact. 2022 Dec 28;21(1):274. doi: 10.1186/s12934-022-02003-z. PMID: 36578077; PMCID: PMC9798599. 3: Czech L, Hermann L, Stöveken N, Richter AA, Höppner A, Smits SHJ, Heider J, Bremer E. Role of the Extremolytes Ectoine and Hydroxyectoine as Stress Protectants and Nutrients: Genetics, Phylogenomics, Biochemistry, and Structural Analysis. Genes (Basel). 2018 Mar 22;9(4):177. doi: 10.3390/genes9040177. PMID: 29565833; PMCID: PMC5924519. 4: Marcos-Rodrigo E, Lebrero R, Muñoz R, Sousa DZ, Cantera S. Syngas biological transformation into hydroxyectoine. Bioresour Technol. 2025 Feb;417:131842. doi: 10.1016/j.biortech.2024.131842. Epub 2024 Nov 19. PMID: 39566695. 5: Qin Z, Li L, Zeng W, Li H, Zhou J, Xu S. High efficiency production of 5-hydroxyectoine using metabolically engineered Escherichia coli. Bioresour Technol. 2024 Dec;413:131493. doi: 10.1016/j.biortech.2024.131493. Epub 2024 Sep 14. PMID: 39284374. 6: Kadaba Srinivasan P, Fet N, Bleilevens C, Afify M, Doorschodt B, Yagi S, van Echten-Deckert G, Tolba RH. Hydroxyectoine ameliorates preservation injury in deceased after cardiac death donors in experimental liver grafts. Ann Transplant. 2014 Apr 14;19:165-73. doi: 10.12659/AOT.889958. PMID: 24727658. 7: Hermann L, Dempwolff F, Steinchen W, Freibert SA, Smits SHJ, Seubert A, Bremer E. The MocR/GabR Ectoine and Hydroxyectoine Catabolism Regulator EnuR: Inducer and DNA Binding. Front Microbiol. 2021 Dec 24;12:764731. doi: 10.3389/fmicb.2021.764731. PMID: 35003002; PMCID: PMC8739950. 8: Nayak PK, Goode M, Chang DP, Rajagopal K. Ectoine and Hydroxyectoine Stabilize Antibodies in Spray-Dried Formulations at Elevated Temperature and during a Freeze/Thaw Process. Mol Pharm. 2020 Sep 8;17(9):3291-3297. doi: 10.1021/acs.molpharmaceut.0c00395. Epub 2020 Jul 30. PMID: 32672979. 9: Argandoña M, Piubeli F, Reina-Bueno M, Nieto JJ, Vargas C. New insights into hydroxyectoine synthesis and its transcriptional regulation in the broad-salt growing halophilic bacterium Chromohalobacter salexigens. Microb Biotechnol. 2021 Jul;14(4):1472-1493. doi: 10.1111/1751-7915.13799. Epub 2021 May 6. PMID: 33955667; PMCID: PMC8313267. 10: Ma Q, Xia L, Wu H, Zhuo M, Yang M, Zhang Y, Tan M, Zhao K, Sun Q, Xu Q, Chen N, Xie X. Metabolic engineering of Escherichia coli for efficient osmotic stress-free production of compatible solute hydroxyectoine. Biotechnol Bioeng. 2022 Jan;119(1):89-101. doi: 10.1002/bit.27952. Epub 2021 Oct 13. PMID: 34612520. 11: Dabous A, Stellavato A, Cimini D, Vassallo V, D'Agostino M, Schiraldi C. A probiotic multi-strain mixture combined with hydroxyectoine improves intestinal barrier function by alleviating inflammation in lipopolysaccharide stimulated differentiated Caco-2 cells. Food Funct. 2024 Nov 25;15(23):11578-11589. doi: 10.1039/d4fo03130j. PMID: 39508078. 12: Moritz KD, Amendt B, Witt EM, Galinski EA. The hydroxyectoine gene cluster of the non-halophilic acidophile Acidiphilium cryptum. Extremophiles. 2015 Jan;19(1):87-99. doi: 10.1007/s00792-014-0687-0. Epub 2014 Aug 21. PMID: 25142158. 13: Yang N, Liu M, Han J, Jiang M, Zeng Y, Liu Y, Xiang H, Zheng Y. Rational engineering of Halomonas salifodinae to enhance hydroxyectoine production under lower-salt conditions. Appl Microbiol Biotechnol. 2024 May 31;108(1):353. doi: 10.1007/s00253-024-13197-0. PMID: 38819481; PMCID: PMC11142988. 14: Tanne C, Golovina EA, Hoekstra FA, Meffert A, Galinski EA. Glass-forming property of hydroxyectoine is the cause of its superior function as a desiccation protectant. Front Microbiol. 2014 Apr 4;5:150. doi: 10.3389/fmicb.2014.00150. PMID: 24772110; PMCID: PMC3983491. 15: Cantera S, Di Benedetto F, Tumulero BF, Sousa DZ. Microbial conversion of carbon dioxide and hydrogen into the fine chemicals hydroxyectoine and ectoine. Bioresour Technol. 2023 Apr;374:128753. doi: 10.1016/j.biortech.2023.128753. Epub 2023 Feb 17. PMID: 36801441. 16: Tsai T, Mueller-Buehl AM, Satgunarajah Y, Kuehn S, Dick HB, Joachim SC. Protective effect of the extremolytes ectoine and hydroxyectoine in a porcine organ culture. Graefes Arch Clin Exp Ophthalmol. 2020 Oct;258(10):2185-2203. doi: 10.1007/s00417-020-04854-x. Epub 2020 Jul 24. Erratum in: Graefes Arch Clin Exp Ophthalmol. 2021 Nov;259(11):3527. doi: 10.1007/s00417-021-05418-3. PMID: 32710140; PMCID: PMC8478759. 17: Yanykin DV, Malferrari M, Rapino S, Venturoli G, Semenov AY, Mamedov MD. Hydroxyectoine protects Mn-depleted photosystem II against photoinhibition acting as a source of electrons. Photosynth Res. 2019 Aug;141(2):165-179. doi: 10.1007/s11120-019-00617-w. Epub 2019 Jan 30. PMID: 30701483. 18: Sahle CJ , Schroer MA , Jeffries CM , Niskanen J . Hydration in aqueous solutions of ectoine and hydroxyectoine. Phys Chem Chem Phys. 2018 Nov 14;20(44):27917-27923. doi: 10.1039/c8cp05308a. PMID: 30379162. 19: Tao P, Li H, Yu Y, Gu J, Liu Y. Ectoine and 5-hydroxyectoine accumulation in the halophile Virgibacillus halodenitrificans PDB-F2 in response to salt stress. Appl Microbiol Biotechnol. 2016 Aug;100(15):6779-6789. doi: 10.1007/s00253-016-7549-x. Epub 2016 Apr 23. PMID: 27106915. 20: Eilert E, Kranz A, Hollenberg CP, Piontek M, Suckow M. Synthesis and release of the bacterial compatible solute 5-hydroxyectoine in Hansenula polymorpha. J Biotechnol. 2013 Aug 20;167(2):85-93. doi: 10.1016/j.jbiotec.2013.02.005. Epub 2013 Mar 4. PMID: 23467000.