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MedKoo Cat#: 525594 | Name: EDHB

Description:

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

EDHB is a pan-PHD inhibitor.

Chemical Structure

EDHB
EDHB
CAS#3943-89-3

Theoretical Analysis

MedKoo Cat#: 525594

Name: EDHB

CAS#: 3943-89-3

Chemical Formula: C18H18O7

Exact Mass: 346.1053

Molecular Weight: 346.34

Elemental Analysis: C, 62.42; H, 5.24; O, 32.34

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
EDHB
IUPAC/Chemical Name
Ethyl-3,4-dihydroxybenzoate; Ethyl protocatechuate
InChi Key
IEWPWVSCXPNIRW-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H18O7/c1-3-11-12(6-7-13(19)16(11)21)18(23)25-15-8-5-10(9-14(15)20)17(22)24-4-2/h5-9,19-21H,3-4H2,1-2H3
SMILES Code
O=C(OCC)C1=CC=C(OC(C2=CC=C(O)C(O)=C2CC)=O)C(O)=C1
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

Preparing Stock Solutions

The following data is based on the product molecular weight 346.34 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: Harnoss JM, Platzer LK, Burhenne J, Radhakrishnan P, Cai J, Strowitzki MJ, Weiss J, Ritter AS, Mollenhauer M, Schmidt T, Ulrich A, Haefeli WE, Schneider M. Prolyl Hydroxylase Inhibition Enhances Liver Regeneration Without Induction of Tumor Growth. Ann Surg. 2017 Apr;265(4):782-791. doi: 10.1097/SLA.0000000000001696. PubMed PMID: 28266966. 2: Nimker C, Singh DP, Saraswat D, Bansal A. Preconditioning with ethyl 3,4-dihydroxybenzoate augments aerobic respiration in rat skeletal muscle. Hypoxia (Auckl). 2016 May 13;4:109-120. eCollection 2016. PubMed PMID: 27800513; PubMed Central PMCID: PMC5085279. 3: Pizzute T, Zhang Y, He F, Pei M. Ascorbate-dependent impact on cell-derived matrix in modulation of stiffness and rejuvenation of infrapatellar fat derived stem cells toward chondrogenesis. Biomed Mater. 2016 Aug 10;11(4):045009. doi: 10.1088/1748-6041/11/4/045009. PubMed PMID: 27508528; PubMed Central PMCID: PMC5004760. 4: Huang M, Paglialunga S, Wong JM, Hoang M, Pillai R, Joseph JW. Role of prolyl hydroxylase domain proteins in the regulation of insulin secretion. Physiol Rep. 2016 Mar;4(5). pii: e12722. doi: 10.14814/phy2.12722. PubMed PMID: 26997627; PubMed Central PMCID: PMC4823601. 5: Harnoss JM, Platzer LK, Burhenne J, Radhakrishnan P, Cai J, Strowitzki MJ, Weiss J, Ritter AS, Mollenhauer M, Schmidt T, Ulrich A, Haefeli WE, Schneider M. Prolyl Hydroxylase Inhibition Enhances Liver Regeneration Without Induction of Tumor Growth. Ann Surg. 2016 Mar 8. [Epub ahead of print] PubMed PMID: 26967635. 6: Li W, Hou G, Zhou D, Lou X, Xu Y, Liu S, Zhao X. The roles of AKR1C1 and AKR1C2 in ethyl-3,4-dihydroxybenzoate induced esophageal squamous cell carcinoma cell death. Oncotarget. 2016 Apr 19;7(16):21542-55. doi: 10.18632/oncotarget.7775. PubMed PMID: 26934124; PubMed Central PMCID: PMC5008304. 7: Singh DP, Nimker C, Paliwal P, Bansal A. Ethyl 3,4-dihydroxybenzoate (EDHB): a prolyl hydroxylase inhibitor attenuates acute hypobaric hypoxia mediated vascular leakage in brain. J Physiol Sci. 2016 Jul;66(4):315-26. doi: 10.1007/s12576-015-0429-9. Epub 2015 Dec 9. PubMed PMID: 26649730. 8: Vasta JD, Andersen KA, Deck KM, Nizzi CP, Eisenstein RS, Raines RT. Selective Inhibition of Collagen Prolyl 4-Hydroxylase in Human Cells. ACS Chem Biol. 2016 Jan 15;11(1):193-9. doi: 10.1021/acschembio.5b00749. Epub 2015 Nov 19. PubMed PMID: 26535807; PubMed Central PMCID: PMC4798942. 9: Abe T, Kitaoka Y, Kikuchi DM, Takeda K, Numata O, Takemasa T. High-intensity interval training-induced metabolic adaptation coupled with an increase in Hif-1α and glycolytic protein expression. J Appl Physiol (1985). 2015 Dec 1;119(11):1297-302. doi: 10.1152/japplphysiol.00499.2015. Epub 2015 Oct 1. PubMed PMID: 26429867. 10: Miklasińska M, Kępa M, Wojtyczka RD, Idzik D, Zdebik A, Orlewska K, Wąsik TJ. Antibacterial Activity of Protocatechuic Acid Ethyl Ester on Staphylococcus aureus Clinical Strains Alone and in Combination with Antistaphylococcal Drugs. Molecules. 2015 Jul 23;20(8):13536-49. doi: 10.3390/molecules200813536. PubMed PMID: 26213908. 11: Nimker C, Kaur G, Revo A, Chaudhary P, Bansal A. Ethyl 3,4-dihydroxy benzoate, a unique preconditioning agent for alleviating hypoxia-mediated oxidative damage in L6 myoblasts cells. J Physiol Sci. 2015 Jan;65(1):77-87. doi: 10.1007/s12576-014-0348-1. Epub 2014 Nov 8. PubMed PMID: 25381174. 12: Fan L, Li J, Yu Z, Dang X, Wang K. Hypoxia-inducible factor prolyl hydroxylase inhibitor prevents steroid-associated osteonecrosis of the femoral head in rabbits by promoting angiogenesis and inhibiting apoptosis. PLoS One. 2014 Sep 22;9(9):e107774. doi: 10.1371/journal.pone.0107774. eCollection 2014. PubMed PMID: 25244080; PubMed Central PMCID: PMC4171501. 13: Kwon BJ, Lee MH, Koo MA, Han JJ, Park JC. Ethyl-3,4-dihydroxybenzoate with a dual function of induction of osteogenic differentiation and inhibition of osteoclast differentiation for bone tissue engineering. Tissue Eng Part A. 2014 Nov;20(21-22):2975-84. doi: 10.1089/ten.TEA.2013.0567. Epub 2014 Jun 23. PubMed PMID: 24784993; PubMed Central PMCID: PMC4229862. 14: Baay-Guzman GJ, Bebenek IG, Zeidler M, Hernandez-Pando R, Vega MI, Garcia-Zepeda EA, Antonio-Andres G, Bonavida B, Riedl M, Kleerup E, Tashkin DP, Hankinson O, Huerta-Yepez S. HIF-1 expression is associated with CCL2 chemokine expression in airway inflammatory cells: implications in allergic airway inflammation. Respir Res. 2012 Jul 23;13:60. doi: 10.1186/1465-9921-13-60. PubMed PMID: 22823210; PubMed Central PMCID: PMC3439306. 15: Huerta-Yepez S, Baay-Guzman GJ, Bebenek IG, Hernandez-Pando R, Vega MI, Chi L, Riedl M, Diaz-Sanchez D, Kleerup E, Tashkin DP, Gonzalez FJ, Bonavida B, Zeidler M, Hankinson O. Hypoxia inducible factor promotes murine allergic airway inflammation and is increased in asthma and rhinitis. Allergy. 2011 Jul;66(7):909-18. doi: 10.1111/j.1398-9995.2011.02594.x. Epub 2011 Apr 26. PubMed PMID: 21517900; PubMed Central PMCID: PMC3107385. 16: May JM, Qu ZC. Chelation of intracellular iron enhances endothelial barrier function: a role for vitamin C? Arch Biochem Biophys. 2010 Aug 15;500(2):162-8. doi: 10.1016/j.abb.2010.05.022. Epub 2010 May 26. PubMed PMID: 20510668; PubMed Central PMCID: PMC2904406. 17: Chu PW, Beart PM, Jones NM. Preconditioning protects against oxidative injury involving hypoxia-inducible factor-1 and vascular endothelial growth factor in cultured astrocytes. Eur J Pharmacol. 2010 May 10;633(1-3):24-32. doi: 10.1016/j.ejphar.2010.02.008. Epub 2010 Feb 11. PubMed PMID: 20153315. 18: Li B, Takeda K, Yokoyama S, Shibahara S. A prolyl-hydroxylase inhibitor, ethyl-3,4-dihydroxybenzoate, induces haem oxygenase-1 expression in human cells through a mechanism independent of hypoxia-inducible factor-1alpha. J Biochem. 2008 Nov;144(5):643-54. doi: 10.1093/jb/mvn115. Epub 2008 Sep 17. PubMed PMID: 18799519. 19: Zhong Z, Ramshesh VK, Rehman H, Currin RT, Sridharan V, Theruvath TP, Kim I, Wright GL, Lemasters JJ. Activation of the oxygen-sensing signal cascade prevents mitochondrial injury after mouse liver ischemia-reperfusion. Am J Physiol Gastrointest Liver Physiol. 2008 Oct;295(4):G823-32. doi: 10.1152/ajpgi.90287.2008. Epub 2008 Sep 4. PubMed PMID: 18772364; PubMed Central PMCID: PMC2575910. 20: Kant R, Diwan V, Jaggi AS, Singh N, Singh D. Remote renal preconditioning-induced cardioprotection: a key role of hypoxia inducible factor-prolyl 4-hydroxylases. Mol Cell Biochem. 2008 May;312(1-2):25-31. doi: 10.1007/s11010-008-9717-5. Epub 2008 Feb 14. PubMed PMID: 18273560.