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MedKoo Cat#: 571048 | Name: Diplopterol

Description:

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

Diplopterol is a biosyntheside from squalene in a cell-free system for Acetobacter pasteurianum. It is a hopanoid that can function as a substitute for sterols.

Chemical Structure

Diplopterol
Diplopterol
CAS#1721-59-1

Theoretical Analysis

MedKoo Cat#: 571048

Name: Diplopterol

CAS#: 1721-59-1

Chemical Formula: C30H52O

Exact Mass: 428.4018

Molecular Weight: 428.75

Elemental Analysis: C, 84.04; H, 12.23; O, 3.73

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
Diplopterol
IUPAC/Chemical Name
22-Hydroxyhopane
InChi Key
PNJBOAVCVAVRGR-INNBTYQQSA-N
InChi Code
InChI=1S/C30H52O/c1-25(2)15-9-16-28(6)22(25)14-19-30(8)24(28)11-10-23-27(5)17-12-20(26(3,4)31)21(27)13-18-29(23,30)7/h20-24,31H,9-19H2,1-8H3/t20-,21-,22?,23+,24+,27-,28-,29+,30+/m0/s1
SMILES Code
CC1(C)CCC[C@]2(C)[C@@]3([H])CC[C@]4([H])[C@@]5(C)CC[C@H](C(C)(O)C)[C@@]([H])5CC[C@](C)4[C@@](C)3CCC12
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 428.75 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: Wu CH, Kong L, Bialecka-Fornal M, Park S, Thompson AL, Kulkarni G, Conway SJ, Newman DK. Quantitative hopanoid analysis enables robust pattern detection and comparison between laboratories. Geobiology. 2015 Jul;13(4):391-407. doi: 10.1111/gbi.12132. Epub 2015 Apr 11. PubMed PMID: 25865768; PubMed Central PMCID: PMC4676935. 2: Babiak Z, Carlisle TL, Holmlund CE. Inhibtion of diplopterol synthesis in Tetrahymena pyriformis by a hypocholesteremic compound. Lipids. 1975 Jul;10(7):437-40. PubMed PMID: 167262. 3: Sáenz JP, Grosser D, Bradley AS, Lagny TJ, Lavrynenko O, Broda M, Simons K. Hopanoids as functional analogues of cholesterol in bacterial membranes. Proc Natl Acad Sci U S A. 2015 Sep 22;112(38):11971-6. doi: 10.1073/pnas.1515607112. Epub 2015 Sep 8. PubMed PMID: 26351677; PubMed Central PMCID: PMC4586864. 4: Caron B, Mark AE, Poger D. Some Like It Hot: The Effect of Sterols and Hopanoids on Lipid Ordering at High Temperature. 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PubMed PMID: 23543500. 9: Lodha TD, Srinivas A, Sasikala C, Ramana CV. Hopanoid inventory of Rhodoplanes spp. Arch Microbiol. 2015 Aug;197(6):861-7. doi: 10.1007/s00203-015-1112-5. Epub 2015 May 3. PubMed PMID: 25935452. 10: Sáenz JP, Sezgin E, Schwille P, Simons K. Functional convergence of hopanoids and sterols in membrane ordering. Proc Natl Acad Sci U S A. 2012 Aug 28;109(35):14236-40. doi: 10.1073/pnas.1212141109. Epub 2012 Aug 14. PubMed PMID: 22893685; PubMed Central PMCID: PMC3435179. 11: Tushar L, Sasikala Ch, Ramana ChV. Draft genome sequence of Rhodomicrobium udaipurense JA643T with special reference to hopanoid biosynthesis. DNA Res. 2014 Dec;21(6):639-47. doi: 10.1093/dnares/dsu026. Epub 2014 Aug 12. PubMed PMID: 25117430; PubMed Central PMCID: PMC4263297. 12: Birgel D, Meister P, Lundberg R, Horath TD, Bontognali TR, Bahniuk AM, de Rezende CE, Vasconcelos C, McKenzie JA. Methanogenesis produces strong 13C enrichment in stromatolites of Lagoa Salgada, Brazil: a modern analogue for Palaeo-/Neoproterozoic stromatolites? Geobiology. 2015 May;13(3):245-66. doi: 10.1111/gbi.12130. Epub 2015 Mar 13. PubMed PMID: 25773379. 13: Rohmer M, Anding C, Ourisson G. Non-specific biosynthesis of hopane triterpenes by a cell-free system from Acetobacter pasteurianum. Eur J Biochem. 1980 Dec;112(3):541-7. PubMed PMID: 7460938. 14: Sultanpuram VR, Lodha TD, Chintalapati VR, Chintalapati S. Cohaesibacter haloalkalitolerans sp. nov., isolated from a soda lake, and emended description of the genus Cohaesibacter. Int J Syst Evol Microbiol. 2013 Nov;63(Pt 11):4271-6. doi: 10.1099/ijs.0.050112-0. Epub 2013 Jun 28. PubMed PMID: 23811140. 15: Kathiravan R, Jegan S, Ganga V, Prabavathy VR, Tushar L, Sasikala Ch, Ramana ChV. Ciceribacter lividus gen. nov., sp. nov., isolated from rhizosphere soil of chick pea (Cicer arietinum L.). Int J Syst Evol Microbiol. 2013 Dec;63(Pt 12):4484-8. doi: 10.1099/ijs.0.049726-0. Epub 2013 Aug 1. PubMed PMID: 23907221. 16: Subhash Y, Sasikala Ch, Ramana ChV. Salinimicrobium sediminis sp. nov., isolated from a deep-sea sediment. Int J Syst Evol Microbiol. 2014 Mar;64(Pt 3):984-8. doi: 10.1099/ijs.0.058149-0. Epub 2013 Dec 18. PubMed PMID: 24425818. 17: Ramana VV, Raj PS, Tushar L, Sasikala Ch, Ramana ChV. Rhodomicrobium udaipurense sp. nov., a psychrotolerant, phototrophic alphaproteobacterium isolated from a freshwater stream. Int J Syst Evol Microbiol. 2013 Jul;63(Pt 7):2684-9. doi: 10.1099/ijs.0.046409-0. Epub 2013 Jan 4. PubMed PMID: 23291882. 18: Raederstorff D, Rohmer M. Polyterpenoids as cholesterol and tetrahymanol surrogates in the ciliate Tetrahymena pyriformis. Biochim Biophys Acta. 1988 May 22;960(2):190-9. PubMed PMID: 3130105. 19: Parag B, Sasikala Ch, Ramana ChV. Molecular and culture dependent characterization of endolithic bacteria in two beach sand samples and description of Rhizobium endolithicum sp. nov. Antonie Van Leeuwenhoek. 2013 Dec;104(6):1235-44. doi: 10.1007/s10482-013-0046-7. Epub 2013 Oct 9. PubMed PMID: 24104485. 20: Yang JH, Kondratyuk TP, Jermihov KC, Marler LE, Qiu X, Choi Y, Cao H, Yu R, Sturdy M, Huang R, Liu Y, Wang LQ, Mesecar AD, van Breemen RB, Pezzuto JM, Fong HH, Chen YG, Zhang HJ. Bioactive compounds from the fern Lepisorus contortus. J Nat Prod. 2011 Feb 25;74(2):129-36. doi: 10.1021/np100373f. Epub 2011 Jan 24. PubMed PMID: 21261296; PubMed Central PMCID: PMC3069126.