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MedKoo Cat#: 581108 | Name: Tingenone

Description:

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

Tingenone is a pentacyclic triterpene, induces peripheral antinociception due to opioidergic activation.

Chemical Structure

Tingenone
CAS#50802-21-6

Theoretical Analysis

MedKoo Cat#: 581108

Name: Tingenone

CAS#: 50802-21-6

Chemical Formula: C28H36O3

Exact Mass: 420.2664

Molecular Weight: 420.59

Elemental Analysis: C, 79.96; H, 8.63; O, 11.41

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
Tingenone; Maitenin; Maytenin; Tingenin A; Tingenon;
IUPAC/Chemical Name
(6bR,8aS,11R,12aR,12bS,14aS)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydropicene-2,10(6bH,9H)-dione
InChi Key
WSTYNZDAOAEEKG-GMGVRFIYSA-N
InChi Code
InChI=1S/C28H36O3/c1-16-13-23-25(3,15-21(16)30)9-11-27(5)22-8-7-18-17(2)24(31)20(29)14-19(18)26(22,4)10-12-28(23,27)6/h7-8,14,16,23,31H,9-13,15H2,1-6H3/t16-,23-,25+,26-,27+,28+/m1/s1
SMILES Code
C1=2[C@@]3(C([C@@]4(CC[C@@]5([C@H]([C@@]4(CC3)C)C[C@H](C(=O)C5)C)C)C)=CC=C1C(=C(O)C(C2)=O)C)C
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 420.59 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: Veloso Cde C, Rodrigues VG, Ferreira RC, Duarte LP, Klein A, Duarte ID, Romero TR, Perez Ade C. Tingenone, a pentacyclic triterpene, induces peripheral antinociception due to opioidergic activation. Planta Med. 2014 Nov;80(17):1615-21. doi: 10.1055/s-0034-1383147. Epub 2014 Oct 22. PubMed PMID: 25338214. 2: de Carvalho Veloso C, Rodrigues VG, Ferreira RC, Duarte LP, Klein A, Duarte ID, Romero TR, de Castro Perez A. Tingenone, a pentacyclic triterpene, induces peripheral antinociception due to NO/cGMP and ATP-sensitive K(+) channels pathway activation in mice. Eur J Pharmacol. 2015 May 15;755:1-5. doi: 10.1016/j.ejphar.2015.02.038. Epub 2015 Mar 5. PubMed PMID: 25748602. 3: Setzer WN, Setzer MC, Hopper AL, Moriarity DM, Lehrman GK, Niekamp KL, Morcomb SM, Bates RB, McClure KJ, Stessman CC, Haber WA. The cytotoxic activity of a Salacia liana species from Monteverde, Costa Rica, is due to a high concentration of tingenone. Planta Med. 1998 Aug;64(6):583. PubMed PMID: 9741306. 4: Goijman SG, Turrens JF, Marini-Bettolo GB, Stoppani AO. Effect of tingenone, a quinonoid triterpene, on growth and macromolecule biosynthesis in Trypanosoma cruzi. Experientia. 1985 May 15;41(5):646-8. PubMed PMID: 3888660. 5: Campanelli AR, D'Alagni M, Marini-Bettolo GB. Spectroscopic evidence for the interaction of tingenone with DNA. FEBS Lett. 1980 Dec 29;122(2):256-60. PubMed PMID: 7202715. 6: Sotanaphun U, Lipipun V, Suttisri R, Bavovada R. Antimicrobial activity and stability of tingenone derivatives. Planta Med. 1999 Jun;65(5):450-2. PubMed PMID: 10418334. 7: Campanelli AR, D'Alagni M, Marini-Bettolo GB, Giglio E. Optical study of tingenone solubilized in aqueous solution of sodium deoxycholate. Farmaco Prat. 1981 Jan;36(1):30-5. PubMed PMID: 7227494. 8: Goijman SG, Turrens JF, Marini-Bettolo GB, Stoppani AO. [Inhibition of growth and macromolecular biosynthesis in Trypanosoma cruzi by natural products. Effects of miconidine and tingenone]. Medicina (B Aires). 1984;44(4):361-70. Spanish. PubMed PMID: 6399926. 9: Monache FD, Bettólo GV, de Lima OG, D'Albuquerque IL, de Barros Coêlho JS. The structure of tingenone, a quinonoid triterpene related to pristimerin. J Chem Soc Perkin 1. 1973;22:2725-8. PubMed PMID: 4799459. 10: Roca-Mézquita C, Graniel-Sabido M, Moo-Puc RE, Leon-Déniz LV, Gamboa-León R, Arjona-Ruiz C, Tun-Garrido J, Mirón-López G, Mena-Rejón GJ. ANTIPROTOZOAL ACTIVITY OF EXTRACTS OF ELAEODENDRON TRICHOTOMUM (CELASTRACEAE). Afr J Tradit Complement Altern Med. 2016 Jul 3;13(4):162-165. doi: 10.21010/ajtcam.v13i4.21. eCollection 2016. PubMed PMID: 28852732; PubMed Central PMCID: PMC5566140. 11: Meneguetti DU, Lima RA, Hurtado FB, Passarini GM, Macedo SR, Barros NB, Oliveira FA, Medeiros PS, Militão JS, Nicolete R, Facundo VA. Screening of the in vitro antileishmanial activities of compounds and secondary metabolites isolated from Maytenus guianensis Klotzsch ex Reissek (Celastraceae) chichuá Amazon. Rev Soc Bras Med Trop. 2016 Sep-Oct;49(5):579-585. doi: 10.1590/0037-8682-0156-2016. PubMed PMID: 27812652. 12: Rodrigues-Filho E, Barros FA, Fernandes JB, Braz-Filho R. Detection and identification of quinonemethide triterpenes in Peritassa campestris by mass spectrometry. Rapid Commun Mass Spectrom. 2002;16(6):627-33. PubMed PMID: 11870901. 13: Yelani T, Hussein AA, Meyer JJ. Isolation and identification of poisonous triterpenoids from Elaeodendron croceum. Nat Prod Res. 2010 Sep;24(15):1418-25. doi: 10.1080/14786410903052399. PubMed PMID: 20234972. 14: Chávez H, Estévez-Braun A, Ravelo AG, González AG. New phenolic and quinone-methide triterpenes from Maytenus amazonica. J Nat Prod. 1999 Mar;62(3):434-6. PubMed PMID: 10096852. 15: Cevatemre B, Botta B, Mori M, Berardozzi S, Ingallina C, Ulukaya E. The plant-derived triterpenoid tingenin B is a potent anticancer agent due to its cytotoxic activity on cancer stem cells of breast cancer in vitro. Chem Biol Interact. 2016 Dec 25;260:248-255. doi: 10.1016/j.cbi.2016.10.001. Epub 2016 Oct 5. PubMed PMID: 27720947. 16: Setzer WN, Holland MT, Bozeman CA, Rozmus GF, Setzer MC, Moriarity DM, Reeb S, Vogler B, Bates RB, Haber WA. Isolation and frontier molecular orbital investigation of bioactive quinone-methide triterpenoids from the bark of Salacia petenensis. Planta Med. 2001 Feb;67(1):65-9. PubMed PMID: 11270725. 17: Veloso CC, Ferreira RCM, Rodrigues VG, Duarte LP, Klein A, Duarte ID, Romero TRL, Perez AC. Tingenone, a pentacyclic triterpene, induces peripheral antinociception due to cannabinoid receptors activation in mice. Inflammopharmacology. 2018 Feb;26(1):227-233. doi: 10.1007/s10787-017-0391-7. Epub 2017 Sep 9. PubMed PMID: 28889355. 18: Quesadas-Rojas M, Mena-Rejón GJ, Cáceres-Castillo D, Cuevas G, Quijano-Quiñones RF. Biogenesis of Triterpene Dimers from Orthoquinones Related to Quinonemethides: Theoretical Study on the Reaction Mechanism. Molecules. 2016 Nov 17;21(11). pii: E1551. PubMed PMID: 27869690. 19: Moreira RR, Carlos IZ, Vilega W. Release of intermediate reactive hydrogen peroxide by macrophage cells activated by natural products. Biol Pharm Bull. 2001 Feb;24(2):201-4. PubMed PMID: 11217094. 20: Ngassapa O, Soejarto DD, Pezzuto JM, Farnsworth NR. Quinone-methide triterpenes and salaspermic acid from Kokoona ochracea. J Nat Prod. 1994 Jan;57(1):1-8. PubMed PMID: 8158155.