MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 565154 | Name: Ingenol 3,20-dibenzoate

Description:

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

Ingenol 3,20-dibenzoate is a natural protein kinase C (PKC) activator which acts as a functional corrector of some LQTS2 mutant channels.

Chemical Structure

Ingenol 3,20-dibenzoate
Ingenol 3,20-dibenzoate
CAS#59086-90-7

Theoretical Analysis

MedKoo Cat#: 565154

Name: Ingenol 3,20-dibenzoate

CAS#: 59086-90-7

Chemical Formula: C34H36O7

Exact Mass: 556.2461

Molecular Weight: 556.66

Elemental Analysis: C, 73.36; H, 6.52; O, 20.12

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Ingenol 3,20-dibenzoate; Ingenol 3,20 dibenzoate; IDB
IUPAC/Chemical Name
((1aR,2S,5R,5aS,6S,9R,10aR)-6-(Benzoyloxy)-5,5a-dihydroxy-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-4-yl)methyl benzoate
InChi Key
GIMKEHNOTHXONN-HNIMUKOUSA-N
InChi Code
InChI=1S/C34H36O7/c1-19-17-33-20(2)15-25-26(32(25,3)4)24(28(33)36)16-23(18-40-30(37)21-11-7-5-8-12-21)27(35)34(33,39)29(19)41-31(38)22-13-9-6-10-14-22/h5-14,16-17,20,24-27,29,35,39H,15,18H2,1-4H3/t20-,24+,25-,26+,27-,29+,33?,34+/m1/s1
SMILES Code
O=C(OCC1=C[C@@](C2=O)([H])[C@@]3([H])[C@@](C3(C)C)([H])C[C@@H](C)C2(C=C(C)[C@@H]4OC(C5=CC=CC=C5)=O)[C@]4(O)[C@@H]1O)C6=CC=CC=C6
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
>3 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 556.66 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: Gong C, Yao C, Xu Z, Ni Z, Zhu X, Wang L, Yan X, Zhou W, Zhu S. Enhancement of NK cell-mediated lysis of non-small lung cancer cells by nPKC activator, ingenol 3,20 dibenzoate. Mol Immunol. 2017 Mar;83:23-32. doi: 10.1016/j.molimm.2017.01.012. Epub 2017 Jan 13. PubMed PMID: 28092804. 2: Oh JG, Chin YW, Kim SJ, Choi JM, Kim SK, Kang HE, Heo TH. Biphasic Effects of Ingenol 3,20-Dibenzoate on the Erythropoietin Receptor: Synergism at Low Doses and Antagonism at High Doses. Mol Pharmacol. 2015 Aug;88(2):392-400. doi: 10.1124/mol.114.097436. Epub 2015 Jun 5. PubMed PMID: 26048958. 3: Racke FK, Baird M, Barth RF, Huo T, Yang W, Gupta N, Weldon M, Rutledge H. Unique in vitro and in vivo thrombopoietic activities of ingenol 3,20 dibenzoate, a Ca(++)-independent protein kinase C isoform agonist. PLoS One. 2012;7(12):e51059. doi: 10.1371/journal.pone.0051059. Epub 2012 Dec 21. PubMed PMID: 23284657; PubMed Central PMCID: PMC3528756. 4: Desmond R, Dunfee A, Racke F, Dunbar CE, Larochelle A. CD9 up-regulation on CD34+ cells with ingenol 3,20-dibenzoate does not improve homing in NSG mice. Blood. 2011 May 26;117(21):5774-6. doi: 10.1182/blood-2011-01-332031. PubMed PMID: 21617010; PubMed Central PMCID: PMC3110034. 5: Tafti BA, Hantash BM. Dual regulation of the cardiac L-type calcium channel in L6 cells by protein kinase C. Cell Calcium. 2008 Dec;44(6):545-53. doi: 10.1016/j.ceca.2008.03.005. Epub 2008 May 5. PubMed PMID: 18456322. 6: Silva VAO, Rosa MN, Martinho O, Tanuri A, Lima JP, Pianowski LF, Reis RM. Modified ingenol semi-synthetic derivatives from Euphorbia tirucalli induce cytotoxicity on a large panel of human cancer cell lines. Invest New Drugs. 2019 Feb 1. doi: 10.1007/s10637-019-00728-0. [Epub ahead of print] PubMed PMID: 30706338. 7: Spivak AM, Bosque A, Balch AH, Smyth D, Martins L, Planelles V. Ex Vivo Bioactivity and HIV-1 Latency Reversal by Ingenol Dibenzoate and Panobinostat in Resting CD4(+) T Cells from Aviremic Patients. Antimicrob Agents Chemother. 2015 Oct;59(10):5984-91. doi: 10.1128/AAC.01077-15. Epub 2015 Jul 13. PubMed PMID: 26169416; PubMed Central PMCID: PMC4576101. 8: Tang Y, Zhang G, Baird M, Racke F, Zhao W. A novel role of CYP2E1 in human megakaryocyte development. In Vivo. 2014 Nov-Dec;28(6):1077-84. PubMed PMID: 25398802. 9: Pandeló José D, Bartholomeeusen K, da Cunha RD, Abreu CM, Glinski J, da Costa TB, Bacchi Rabay AF, Pianowski Filho LF, Dudycz LW, Ranga U, Peterlin BM, Pianowski LF, Tanuri A, Aguiar RS. Reactivation of latent HIV-1 by new semi-synthetic ingenol esters. Virology. 2014 Aug;462-463:328-39. doi: 10.1016/j.virol.2014.05.033. Epub 2014 Jul 9. PubMed PMID: 25014309; PubMed Central PMCID: PMC4383768. 10: Wang W, Cui Q, Li Y, Li B, Yang X, Cui L, Jin H, Qu L. The role of ERK-1/2 in the N/OFQ-induced inhibition of delayed rectifier potassium currents. Biochem Biophys Res Commun. 2010 Apr 16;394(4):1058-62. doi: 10.1016/j.bbrc.2010.03.123. Epub 2010 Mar 21. PubMed PMID: 20331962. 11: Poole DP, Matsuyama H, Nguyen TV, Eriksson EM, Fowler CJ, Furness JB. Inflammation and inflammatory agents activate protein kinase C epsilon translocation and excite guinea-pig submucosal neurons. Gastroenterology. 2007 Oct;133(4):1229-39. Epub 2007 Jul 10. PubMed PMID: 17765238. 12: Poole DP, Furness JB. PKC delta-isoform translocation and enhancement of tonic contractions of gastrointestinal smooth muscle. Am J Physiol Gastrointest Liver Physiol. 2007 Mar;292(3):G887-98. Epub 2006 Dec 7. PubMed PMID: 17158259. 13: Tsao WC, Wu HM, Chi KH, Chang YH, Lin WW. Proteasome inhibitors induce peroxisome proliferator-activated receptor transactivation through RXR accumulation and a protein kinase C-dependent pathway. Exp Cell Res. 2005 Mar 10;304(1):234-43. Epub 2004 Dec 10. PubMed PMID: 15707588. 14: Blanco-Molina M, Tron GC, Macho A, Lucena C, Calzado MA, Muñoz E, Appendino G. Ingenol esters induce apoptosis in Jurkat cells through an AP-1 and NF-kappaB independent pathway. Chem Biol. 2001 Aug;8(8):767-78. PubMed PMID: 11514226. 15: Weller SG, Klein IK, Penington RC, Karnes WE Jr. Distinct protein kinase C isozymes signal mitogenesis and apoptosis in human colon cancer cells. Gastroenterology. 1999 Oct;117(4):848-57. PubMed PMID: 10500067.

View History

Lavanducyanin

Lavanducyanin

SC 19886

SC 19886

GRP-156784

GRP-156784

Bcr-Abl-IN-Y9

Bcr-Abl-IN-Y9

BDF5

BDF5

Glucurolactone

Glucurolactone