WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H585418
CAS#: 62994-47-2
Description: Warburganal is a dialdehyde sesquiterpene isolated from East African Warburgia plants that shows antifungal activity.
Hodoodo Cat#: H585418
Name: Warburganal
CAS#: 62994-47-2
Chemical Formula: C15H22O3
Exact Mass: 250.16
Molecular Weight: 250.338
Elemental Analysis: C, 71.97; H, 8.86; O, 19.17
This product is not in stock, which may be available by custom synthesis.
For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge).
Quote less than 1g will not be provided. To request quote, please email to sales @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.
Synonym: Warburganal
IUPAC/Chemical Name: (1S,4aS,8aS)-1-hydroxy-5,5,8a-trimethyl-4a,6,7,8-tetrahydro-4H-naphthalene-1,2-dicarbaldehyde
InChi Key: QGMWDUUHVVLHNP-AEGPPILISA-N
InChi Code: InChI=1S/C15H22O3/c1-13(2)7-4-8-14(3)12(13)6-5-11(9-16)15(14,18)10-17/h5,9-10,12,18H,4,6-8H2,1-3H3/t12-,14-,15+/m0/s1
SMILES Code: O=C[C@@]1(O)C(C=O)=CC[C@@]2([H])C(C)(C)CCC[C@]12C
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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 250.34 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Mathie K, Lainer J, Spreng S, Dawid C, Andersson DA, Bevan S, Hofmann T. Structure-Pungency Relationships and TRP Channel Activation of Drimane Sesquiterpenes in Tasmanian Pepper (Tasmannia lanceolata). J Agric Food Chem. 2017 Jul 19;65(28):5700-5712. doi: 10.1021/acs.jafc.7b02356. Epub 2017 Jul 7. PubMed PMID: 28657737.
2: Liu M, Kipanga P, Mai AH, Dhondt I, Braeckman BP, De Borggraeve W, Luyten W. Bioassay-guided isolation of three anthelmintic compounds from Warburgia ugandensis Sprague subspecies ugandensis, and the mechanism of action of polygodial. Int J Parasitol. 2018 Sep;48(11):833-844. doi: 10.1016/j.ijpara.2017.11.009. Epub 2018 Jul 18. PubMed PMID: 30031002.
3: Prinsloo G, Marokane CK, Street RA. Anti-HIV activity of southern African plants: Current developments, phytochemistry and future research. J Ethnopharmacol. 2018 Jan 10;210:133-155. doi: 10.1016/j.jep.2017.08.005. Epub 2017 Aug 12. Review. PubMed PMID: 28807850.
4: Taniguchi M, Adachi T, Haraguchi H, Oi S, Kubo I. Physiological activity of warburganal and its reactivity with sulfhydryl groups. J Biochem. 1983 Jul;94(1):149-54. PubMed PMID: 6352692.
5: Kipanga PN, Liu M, Panda SK, Mai AH, Veryser C, Van Puyvelde L, De Borggraeve WM, Van Dijck P, Matasyoh J, Luyten W. Biofilm inhibiting properties of compounds from the leaves of Warburgia ugandensis Sprague subsp ugandensis against Candida and staphylococcal biofilms. J Ethnopharmacol. 2020 Feb 10;248:112352. doi: 10.1016/j.jep.2019.112352. Epub 2019 Oct 30. PubMed PMID: 31676401.
6: Okello D, Kang Y. Ethnopharmacological Potentials of Warburgia ugandensis on Antimicrobial Activities. Chin J Integr Med. 2019 Dec 17. doi: 10.1007/s11655-019-3042-6. [Epub ahead of print] Review. PubMed PMID: 31848891.
7: Leonard CM, Viljoen AM. Warburgia: a comprehensive review of the botany, traditional uses and phytochemistry. J Ethnopharmacol. 2015 May 13;165:260-85. doi: 10.1016/j.jep.2015.02.021. Epub 2015 Feb 17. Review. PubMed PMID: 25698247.
8: Fritz GL, Mills GD Jr, Warthen JD Jr, Waters RM. Reimer-Tiemann adducts as potential insect antifeedant agents Reviewing the structure-activity relationship theory of the antifeedant, warburganal. J Chem Ecol. 1989 Dec;15(12):2607-23. doi: 10.1007/BF01014720. PubMed PMID: 24271675.
9: Barrero AF, Cortés M, Manzaneda EA, Cabrera E, Chahboun R, Lara M, Rivas AR. Synthesis of 11,12-epoxydrim-8,12-en-11-ol, 11,12-diacetoxydrimane, and warburganal from (-)-sclareol. J Nat Prod. 1999 Nov;62(11):1488-91. PubMed PMID: 10579858.
10: Kubo I, Himejima M. Potentiation of antifungal activity of sesquiterpene dialdehydes against Candida albicans and two other fungi. Experientia. 1992 Dec 1;48(11-12):1162-4. PubMed PMID: 1473583.
11: Inocente EA, Nguyen B, Manwill PK, Benatrehina A, Kweka E, Wu S, Cheng X, Rakotondraibe LH, Piermarini PM. Insecticidal and Antifeedant Activities of Malagasy Medicinal Plant (Cinnamosma sp.) Extracts and Drimane-Type Sesquiterpenes against Aedes aegypti Mosquitoes. Insects. 2019 Oct 25;10(11). pii: E373. doi: 10.3390/insects10110373. PubMed PMID: 31731570; PubMed Central PMCID: PMC6920793.
12: Mecchi MC, Lago JH. Chemical constituents derived from Drimys brasiliensis Miers (Winteraceae). Nat Prod Res. 2013 Oct;27(20):1927-9. doi: 10.1080/14786419.2013.782491. Epub 2013 Mar 28. PubMed PMID: 23537128.
13: Stampf JL, Benezra C, Asakawa Y. Stereospecificity of allergic contact dermatitis (ACD) to enantiomers. Part III. experimentally induced ACD to a natural sesquiterpene dialdehyde, polygodial in guinea pigs. Arch Dermatol Res. 1982;274(3-4):277-81. PubMed PMID: 6891888.
14: Xu M, Litaudon M, Krief S, Martin MT, Kasenene J, Kiremire B, Dumontet V, Guéritte F. Ugandenial A, a new drimane-type sesquiterpenoid from Warburgia ugandensis. Molecules. 2009 Sep 28;14(10):3844-50. doi: 10.3390/molecules14103844. PubMed PMID: 19924033; PubMed Central PMCID: PMC6255255.
15: Rugutt JK, Ngigi AN, Rugutt KJ, Ndalut PK. Native Kenyan plants as possible alternatives to methyl bromide in soil fumigation. Phytomedicine. 2006 Sep;13(8):576-83. Epub 2005 Jun 24. PubMed PMID: 16920513.
16: Ley SV. Synthesis of antifeedants for insects: novel behaviour-modifying chemicals from plants. Ciba Found Symp. 1990;154:80-7; discussion 87-98. Review. PubMed PMID: 2086043.
17: Asakawa Y, Dawson GW, Griffiths DC, Lallemand JY, Ley SV, Mori K, Mudd A, Pezechk-Leclaire M, Pickett JA, Watanabe H, Woodcock CM, Zhong-Ning Z. Activity of drimane antifeedants and related compounds against aphids, and comparative biological effects and chemical reactivity of (-)- and (+)-polygodial. J Chem Ecol. 1988 Oct;14(10):1845-55. doi: 10.1007/BF01013481. PubMed PMID: 24277098.
18: Kiso T, Fujita K, Ping X, Tanaka T, Taniguchi M. Screening for microtubule-disrupting antifungal agents by using a mitotic-arrest mutant of Aspergillus nidulans and novel action of phenylalanine derivatives accompanying tubulin loss. Antimicrob Agents Chemother. 2004 May;48(5):1739-48. PubMed PMID: 15105129; PubMed Central PMCID: PMC400532.
19: Rodilla JM, Díez D, Urones JG, Rocha PM. From labdanes to drimanes. Degradation of the side chain of dihydrozamoranic acid. Molecules. 2004 Apr 30;9(5):300-22. PubMed PMID: 18007433; PubMed Central PMCID: PMC6147500.
