WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 463978
CAS#: 54706-99-9
Description: 20-Deoxyingenol is a diterpenoid that has been found in E. kansui and has antioxidant and osteoprotective activities. It inhibits oxidative stress-induced decreases in autophagic flux and apoptosis in isolated mouse chondrocytes when used at a concentration of 10 mM.2 20-Deoxyingenol reduces bone erosion and cartilage calcification in joints in a mouse model of injury-induced osteoarthritis.
MedKoo Cat#: 463978
Name: 20-Deoxyingenol
CAS#: 54706-99-9
Chemical Formula: C20H28O4
Exact Mass: 332.1988
Molecular Weight: 332.44
Elemental Analysis: C, 72.26; H, 8.49; O, 19.25
Synonym: 20-Deoxyingenol; 20 Deoxyingenol;
IUPAC/Chemical Name: (1aR,2R,5R,5aS,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,4,7,9-pentamethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one
InChi Key: FOSYZKSOJUQLTD-VCQBTUPJSA-N
InChi Code: InChI=1S/C20H28O4/c1-9-6-12-14-13(18(14,4)5)7-11(3)19(17(12)23)8-10(2)16(22)20(19,24)15(9)21/h6,8,11-16,21-22,24H,7H2,1-5H3/t11-,12-,13-,14+,15-,16+,19+,20+/m1/s1
SMILES Code: O[C@H]([C@]1([C@H](O)C(C)=C[C@H]([C@]2([H])C3(C)C)C4=O)O)C(C)=C[C@@]14[C@H](C)C[C@]23[H]
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
The following data is based on the product molecular weight 332.44 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 |
1: Gu M, Jin J, Ren C, Chen X, Pan Z, Wu Y, Tian N, Sun L, Wu A, Gao W, Zhou Y, Lin Z, Zhang X. 20-Deoxyingenol alleviates osteoarthritis by activating TFEB in chondrocytes. Pharmacol Res. 2021 Jan 15;165:105361. doi: 10.1016/j.phrs.2020.105361. Epub ahead of print. PMID: 33460793.
2: Zhou SK, Zhang Y, Ju YH, Zhang Q, Luo D, Cao YD, Yao WF, Tang YP, Zhang L. Comparison of content-toxicity-activity of six ingenane-type diterpenoids between Euphorbia kansui before and after stir-fried with vinegar by using UFLC- MS/MS, zebrafish embryos and HT-29 cells. J Pharm Biomed Anal. 2021 Feb 20;195:113828. doi: 10.1016/j.jpba.2020.113828. Epub 2020 Dec 7. PMID: 33349474.
3: Xu Z, Zhu X, Su L, Zou C, Chen X, Hou Y, Gong C, Ng W, Ni Z, Wang L, Yan X, Zhu Y, Jiao X, Yao C, Zhu S. A high-throughput assay for screening natural products that boost NK cell-mediated killing of cancer cells. Pharm Biol. 2020 Dec;58(1):357-366. doi: 10.1080/13880209.2020.1748661. PMID: 32356467; PMCID: PMC7241510.
4: Wei XF, Gan CY, Cui J, Luo YY, Cai XF, Yuan Y, Shen J, Li ZY, Zhang WL, Long QX, Hu Y, Chen J, Tang N, Guo H, Huang AL, Hu JL. Identification of Compounds Targeting Hepatitis B Virus Core Protein Dimerization through a Split Luciferase Complementation Assay. Antimicrob Agents Chemother. 2018 Nov 26;62(12):e01302-18. doi: 10.1128/AAC.01302-18. PMID: 30224531; PMCID: PMC6256781.
5: Zhang Q, Zhang KC, Lou JW, Guo SC, Zhang Y, Yao WF, Tang YP, Wu JH, Zhang L. Simultaneous quantification of twelve compounds in ethyl acetate extracts of Euphorbia kansui before and after fry-baked with vinegar by UPLC-MS/MS and its toxic effect on zebrafish. J Pharm Biomed Anal. 2018 Jun 5;155:169-176. doi: 10.1016/j.jpba.2018.03.035. Epub 2018 Apr 3. PMID: 29631077.
6: Wu YQ, Cao Y, Liu X, Cheng ZH. Regio- and stereo-selective hydroxylations of ingenane diterpenoids by Mortierella ramanniana and Gibberella fujikuroi. Chin J Nat Med. 2016 Dec;14(12):939-945. doi: 10.1016/S1875-5364(17)30020-1. PMID: 28262122.
7: Shu X, Jiang XW, Cheng BC, Ma SC, Chen GY, Yu ZL. Ultra-performance liquid chromatography-quadrupole/time-of-flight mass spectrometry analysis of the impact of processing on toxic components of Kansui Radix. BMC Complement Altern Med. 2016 Feb 24;16:73. doi: 10.1186/s12906-016-1039-7. PMID: 26912002; PMCID: PMC4765025.
8: Zhang L, Gao L, Li Z, Yan X, Yang Y, Tang Y, Cao Y, Ding A. Bio-guided isolation of the cytotoxic terpenoids from the roots of Euphorbia kansui against human normal cell lines L-O2 and GES-1. Int J Mol Sci. 2012;13(9):11247-59. doi: 10.3390/ijms130911247. Epub 2012 Sep 10. PMID: 23109850; PMCID: PMC3472742.
9: Shu X, Yu L, Tang Y, Zhang L, Ding A, Luo D, Duan JA, Shen X. Bioassay-guided separation of the proinflammatory constituents from the roots of Euphorbia kansui. J Nat Med. 2010 Jan;64(1):98-103. doi: 10.1007/s11418-009-0366-0. Epub 2009 Oct 21. PMID: 19844773.
10: Li CF, Wang JH, Cong Y, Li X. A new diterpene from the processed roots of Euphorbia Kansui. J Asian Nat Prod Res. 2008 Jan-Feb;10(1-2):101-4. doi: 10.1080/10286020600782496. PMID: 18253876.
11: Nickel A, Maruyama T, Tang H, Murphy PD, Greene B, Yusuff N, Wood JL. Total synthesis of ingenol. J Am Chem Soc. 2004 Dec 22;126(50):16300-1. doi: 10.1021/ja044123l. PMID: 15600313.
12: Wang LY, Wang NL, Yao XS, Miyata S, Kitanaka S. Diterpenes from the roots of Euphorbia kansui and their in vitro effects on the cell division of Xenopus (part 2). Chem Pharm Bull (Tokyo). 2003 Aug;51(8):935-41. doi: 10.1248/cpb.51.935. PMID: 12913231.
13: Zayed SM, Farghaly M, Soliman SM, Gotta H, Sorg B, Hecker E. Dietary cancer risk from conditional cancerogens (tumor promoters) in produce of livestock fed on species of spurge (Euphorbiaceae). V. Skin irriitant and tumor-promoting diterpene ester toxins of the tigliane and ingenane type in the herbs Euphorbia nubica and Euphorbia helioscopia contaminating fodder of livestock. J Cancer Res Clin Oncol. 2001 Jan;127(1):40-7. doi: 10.1007/s004320000214. PMID: 11206270.
14: Zayed SM, Farghaly M, Taha H, Gminski R, Hecker E. Dietary cancer risk from conditional cancerogens in produce of livestock fed on species of spurge (Euphorbiaceae). III. Milk of lactating goats fed on the skin irritant herb Euphorbia peplus is polluted by tumor promoters of the ingenane diterpene ester type. J Cancer Res Clin Oncol. 1998;124(6):301-6. doi: 10.1007/s004320050173. PMID: 9692836.
15: Zayed SM, Farghaly M, Taha H, Gotta H, Hecker E. Dietary cancer risk conditional cancerogens in produce of livestock fed on species of spurge (Euphorbiaceae). I. Skin irritant and tumor-promoting ingenane-type diterpene esters in E. peplus, one of several herbaceous Euphorbia species contaminating fodder of livestock. J Cancer Res Clin Oncol. 1998;124(3-4):131-40. doi: 10.1007/s004320050146. Erratum in: J Cancer Res Clin Oncol 1998;124(6):351. PMID: 9619738.
16: Falsone G, Crea AE, Noack EA. Uber Inhaltsstoffe von Euphorbiaceae, 7. Mitt. 20-Desoxyingenolmonoester und Ingenoldiester aus Euphorbia biglandulosa Desf [Constituents of Euphorbiaceae, 7. 20-Deoxyingenol Monoesters and ingenol diesters from Euphorbia biglandulosa Desf]. Arch Pharm (Weinheim). 1982 Dec;315(12):1026-32. German. doi: 10.1002/ardp.19823151209. PMID: 7159190.
17: Sayed MD, Riszk A, Hammouda FM, El-Missiry MM, Williamson EM, Evans FJ. Constituents of Egyptian Euphorbiaceae. IX. Irritant and cytotoxic ingenane esters from Euphorbia paralias L. Experientia. 1980 Oct 15;36(10):1206-7. doi: 10.1007/BF01976131. PMID: 7418805.
