Netzahualcoyonol

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MedKoo CAT#: 581112

CAS#: 113579-07-0

Description: Netzahualcoyonol, the crude dichloromethane bark extract of Salacia petenensis (Hippocrateaceae) shows antibacterial and cytotoxic activity. Bioactivity-directed separation led to the isolation of tingenone and netzahualcoyonol as the biologically active materials. Also isolated from the extract were 3-methoxyfriedel-2-en-1-one (a new natural product) and 29-hydroxyfriedelan-3-one. The molecular orbital calculations suggest that a possible mode of cytotoxic action of quinone-methide triterpenoids involves quasi-intercalative interaction of the compounds with DNA followed by nucleophilic addition of the DNA base to carbon-6 of the triterpenoid.


Price and Availability

Size Price Shipping out time Quantity
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Pricing updated 2020-10-29. Prices are subject to change without notice.

Netzahualcoyonol is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 581112
Name: Netzahualcoyonol
CAS#: 113579-07-0
Chemical Formula: C30H38O5
Exact Mass: 478.2719
Molecular Weight: 478.63
Elemental Analysis: C, 75.28; H, 8.00; O, 16.71


Synonym: Netzahualcoyonol;

IUPAC/Chemical Name: methyl (2R,3R,4aS,12bR,14aS,14bS)-3,10-dihydroxy-2,4a,6,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,11,12b,13,14,14a,14b-dodecahydropicene-2-carboxylate

InChi Key: AKILTDMBUDIAST-SMVJIKPISA-N

InChi Code: InChI=1S/C30H38O5/c1-16-13-27(3)15-23(32)30(6,26(34)35-7)14-22(27)29(5)11-10-28(4)19(24(16)29)9-8-18-17(2)25(33)21(31)12-20(18)28/h8-9,12,22-23,32-33H,10-11,13-15H2,1-7H3/t22-,23+,27-,28-,29-,30+/m0/s1

SMILES Code: O[C@H](C1)[C@](C)(C(OC)=O)C[C@H]2[C@@]1(C)CC(C)=C3[C@@]2(C)CC[C@](C)(C4=C5)C3=CC=C4C(C)=C(O)C5=O


Technical Data

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


References

1: 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.