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MedKoo Cat#: 328921 | Name: Enoxolone

Description:

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

Enoxolone, also known as Glycyrrhetic acid, is an 11β-hydroxysteroid dehydrogenase inhibitor used to treat inflammation. Enoxolone is used topically for allergic or infectious skin inflammation and orally for its aldosterone effects in electrolyte regulation.

Chemical Structure

Enoxolone
Enoxolone
CAS#471-53-4

Theoretical Analysis

MedKoo Cat#: 328921

Name: Enoxolone

CAS#: 471-53-4

Chemical Formula: C30H46O4

Exact Mass: 470.3396

Molecular Weight: 470.69

Elemental Analysis: C, 76.55; H, 9.85; O, 13.60

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
Enoxolone; Glycyrrhetic acid; BRN 2229654; BRN-2229654; BRN2229654; NSC 35347; NSC-35347; NSC35347
IUPAC/Chemical Name
(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid
InChi Key
MPDGHEJMBKOTSU-YKLVYJNSSA-N
InChi Code
InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1
SMILES Code
CC(C)([C@](CC[C@@]([C@@]1(CC[C@]2(CC[C@](C(O)=O)(C[C@]2(C1=C3)[H])C)C)C)4C)5[H])[C@@H](O)CC[C@]5(C)[C@@]4([H])C3=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

Preparing Stock Solutions

The following data is based on the product molecular weight 470.69 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: Fan R, Li N, Xu H, Xiang J, Wang L, Gao Y. The mechanism of hydrothermal hydrolysis for glycyrrhizic acid into glycyrrhetinic acid and glycyrrhetinic acid 3-O-mono-β-D-glucuronide in subcritical water. Food Chem. 2016 Jan 1;190:912-21. doi: 10.1016/j.foodchem.2015.06.039. Epub 2015 Jun 16. PubMed PMID: 26213056. 2: Yang J, Xi K, Gui Y, Wang Y, Zhang F, Ma C, Hong H, Liu X, Meng N, Zhang X. [The effect of 18β-sodium glycyrrhetinic acid on the nasal mucosa epithelial cilia in rat models of allergic rhinitis]. Lin Chung Er Bi Yan Hou Tou Jing Wai Ke Za Zhi. 2015 Dec;29(23):2060-4. Chinese. PubMed PMID: 27101679. 3: Ma Y, Xie D, Wang ZH, Dai JG, An XQ, Gu ZY. [Microbial transformation of glycyrrhetinic acid by Cunninghamella blakesleeana]. Zhongguo Zhong Yao Za Zhi. 2015 Nov;40(21):4212-7. Chinese. PubMed PMID: 27071259. 4: Luo J, Liu M, Wu X, Dou Y, Xia Y, Dai Y, Wei Z. DGAEE, a newly synthesized derivative of glycyrrhetinic acid, potently attenuates mouse septic shock via its main metabolite DGA in an IL-10-dependent manner. Int Immunopharmacol. 2015 Dec;29(2):583-90. doi: 10.1016/j.intimp.2015.09.025. Epub 2015 Oct 9. PubMed PMID: 26456500. 5: Lekar AV, Borisenko SN, Vetrova EV, Filonova OV, Maksimenko EV, Borisenko NI, Minkin VI. Study of an Acid-Free Technique for the Preparation of Glycyrrhetinic Acid from Ammonium Glycyrrhizinate in Subcritical Water. Nat Prod Commun. 2015 Nov;10(11):1801-3. PubMed PMID: 26749800. 6: Zhang L, Zhou JP, Yao J. Improved anti-tumor activity and safety profile of a paclitaxel-loaded glycyrrhetinic acid-graft-hyaluronic acid conjugate as a synergistically targeted drug delivery system. Chin J Nat Med. 2015 Dec;13(12):915-24. doi: 10.1016/S1875-5364(15)30097-2. PubMed PMID: 26721710. 7: Huang LR, Hao XJ, Li QJ, Wang DP, Zhang JX, Luo H, Yang XS. 18β-Glycyrrhetinic Acid Derivatives Possessing a Trihydroxylated A Ring Are Potent Gram-Positive Antibacterial Agents. J Nat Prod. 2016 Apr 22;79(4):721-31. doi: 10.1021/acs.jnatprod.5b00641. Epub 2016 Feb 29. PubMed PMID: 26928299. 8: Wang H, Zhang G, Sui H, Liu Y, Park K, Wang W. Comparative studies on the properties of glycyrrhetinic acid-loaded PLGA microparticles prepared by emulsion and template methods. Int J Pharm. 2015 Dec 30;496(2):723-31. doi: 10.1016/j.ijpharm.2015.11.018. Epub 2015 Nov 12. PubMed PMID: 26581771. 9: Lv QL, Wang GH, Chen SH, Hu L, Zhang X, Ying G, Qin CZ, Zhou HH. In Vitro and in Vivo Inhibitory Effects of Glycyrrhetinic Acid in Mice and Human Cytochrome P450 3A4. Int J Environ Res Public Health. 2015 Dec 25;13(1):84. doi: 10.3390/ijerph13010084. PubMed PMID: 26712778; PubMed Central PMCID: PMC4730475. 10: Zhang J, Zhang M, Ji J, Fang X, Pan X, Wang Y, Wu C, Chen M. Glycyrrhetinic Acid-Mediated Polymeric Drug Delivery Targeting the Acidic Microenvironment of Hepatocellular Carcinoma. Pharm Res. 2015 Oct;32(10):3376-90. doi: 10.1007/s11095-015-1714-2. Epub 2015 Jul 7. PubMed PMID: 26148773. 11: Darvishi B, Manoochehri S, Esfandyari-Manesh M, Samadi N, Amini M, Atyabi F, Dinarvand R. Enhanced Cellular Cytotoxicity and Antibacterial Activity of 18-β-Glycyrrhetinic Acid by Albumin-conjugated PLGA Nanoparticles. Drug Res (Stuttg). 2015 Dec;65(12):617-23. doi: 10.1055/s-0034-1390487. Epub 2015 Jan 21. PubMed PMID: 25607747. 12: Zhang H, Huang Q, Zhai J, Zhao YN, Zhang LP, Chen YY, Zhang RW, Li Q, Hu XP. Structural basis for 18-β-glycyrrhetinic acid as a novel non-GSH analog glyoxalase I inhibitor. Acta Pharmacol Sin. 2015 Sep;36(9):1145-50. doi: 10.1038/aps.2015.59. Epub 2015 Aug 17. PubMed PMID: 26279158; PubMed Central PMCID: PMC4561975. 13: Tang ZH, Zhang LL, Li T, Lu JH, Ma DL, Leung CH, Chen XP, Jiang HL, Wang YT, Lu JJ. Glycyrrhetinic acid induces cytoprotective autophagy via the inositol-requiring enzyme 1α-c-Jun N-terminal kinase cascade in non-small cell lung cancer cells. Oncotarget. 2015 Dec 22;6(41):43911-26. doi: 10.18632/oncotarget.6084. PubMed PMID: 26549806; PubMed Central PMCID: PMC4791276. 14: Zhou J, Cai W, Jin M, Xu J, Wang Y, Xiao Y, Hao L, Wang B, Zhang Y, Han J, Huang R. 18β-glycyrrhetinic acid suppresses experimental autoimmune encephalomyelitis through inhibition of microglia activation and promotion of remyelination. Sci Rep. 2015 Sep 2;5:13713. doi: 10.1038/srep13713. PubMed PMID: 26329786; PubMed Central PMCID: PMC4557075. 15: Du H, Liu M, Yang X, Zhai G. The role of glycyrrhetinic acid modification on preparation and evaluation of quercetin-loaded chitosan-based self-aggregates. J Colloid Interface Sci. 2015 Dec 15;460:87-96. doi: 10.1016/j.jcis.2015.08.049. Epub 2015 Aug 24. PubMed PMID: 26319324.