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MedKoo Cat#: 584611 | Name: Lubimin

Description:

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

Lubimin is a phytoalexin that may potentially have antineoplastic properties.

Chemical Structure

Lubimin
Lubimin
CAS#35951-50-9

Theoretical Analysis

MedKoo Cat#: 584611

Name: Lubimin

CAS#: 35951-50-9

Chemical Formula: C15H24O2

Exact Mass: 236.1776

Molecular Weight: 236.36

Elemental Analysis: C, 76.23; H, 10.24; O, 13.54

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
Lubimin
IUPAC/Chemical Name
Spiro(4.5)decane-6-carboxaldehyde, 8-hydroxy-10-methyl-2-(1-methylethenyl)-, (5S-(5alpha(S*),6beta,8beta,10beta))-
InChi Key
CEVNHRPKRNTGKO-OIYCOIKZSA-N
InChi Code
InChI=1S/C15H24O2/c1-10(2)12-4-5-15(8-12)11(3)6-14(17)7-13(15)9-16/h9,11-14,17H,1,4-8H2,2-3H3/t11-,12?,13-,14+,15+/m1/s1
SMILES Code
O=C[C@@H](C[C@@H](O)C[C@H]1C)[C@@]21CCC(C(C)=C)C2
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 236.36 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: Watanabe A, Toshima H, Nagase H, Nagaoka T, Yoshihara T. Structural confirmation of 15-norlubiminol and 15-norepilubiminol, isolated from Solanum aethiopicum, by chemical conversion from lubimin and epilubimin, and their antifungal activity. Biosci Biotechnol Biochem. 2001 Aug;65(8):1805-11. PubMed PMID: 11577721. 2: Skinnider L, Stoessl A. The effect of the phytoalexins, lubimin, (-)-maackiain, pinosylvin, and the related compounds dehydroloroglossol and hordatine M on human lymphoblastoid cell lines. Experientia. 1986 May 15;42(5):568-70. PubMed PMID: 3709764. 3: Yoshioka H, Sugie K, Park HJ, Maeda H, Tsuda N, Kawakita K, Doke N. Induction of plant gp91 phox homolog by fungal cell wall, arachidonic acid, and salicylic acid in potato. Mol Plant Microbe Interact. 2001 Jun;14(6):725-36. PubMed PMID: 11386368. 4: Nagaoka T, Goto K, Watanabe A, Sakata Y, Yoshihara T. Sesquiterpenoids in root exudates of Solanum aethiopicum. Z Naturforsch C. 2001 Sep-Oct;56(9-10):707-13. PubMed PMID: 11724373. 5: Zacharius RM, Kalan EB, Kimoto WI. Biotransformation of potato stress metabolites rishitin, lubimin, and 15-dihydro lubimin by potato and soybean cell cultures. Plant Cell Rep. 1985 Feb;4(1):1-3. doi: 10.1007/BF00285491. PubMed PMID: 24253632. 6: Kuroyanagi M, Arakawa T, Mikami Y, Yoshida K, Kawahar N, Hayashi T, Ishimaru H. Phytoalexins from hairy roots of Hyoscyamus albus treated with methyl jasmonate. J Nat Prod. 1998 Dec;61(12):1516-9. PubMed PMID: 9868154. 7: Stermer BA, Bostock RM. Involvement of 3-hydroxy-3-methylglutaryl coenzyme a reductase in the regulation of sesquiterpenoid phytoalexin synthesis in potato. Plant Physiol. 1987 Jun;84(2):404-8. PubMed PMID: 16665452; PubMed Central PMCID: PMC1056592. 8: Whitehead IM, Atkinson AL, Threlfall DR. Studies on the biosynthesis and metabolism of the phytoalexin lubimin and related compounds in Datura stramonium L. Planta. 1990 Aug;182(1):81-8. doi: 10.1007/BF00239988. PubMed PMID: 24197002. 9: Preisig CL, Kuć JA. Arachidonic acid-related elicitors of the hypersensitive response in potato and enhancement of their activities by glucans from Phytophthora infestans (Mont.) deBary. Arch Biochem Biophys. 1985 Jan;236(1):379-89. PubMed PMID: 3966802. 10: Nagase H, Nagaoka T, Watanabe A, Sakata Y, Yoshihara T. Sesquiterpenoids from the roots of Solanum aethiopicum. Z Naturforsch C. 2001 Mar-Apr;56(3-4):181-7. PubMed PMID: 11371006. 11: Zook MN, Rush JS, Kuć JA. A role for ca in the elicitation of rishitin and lubimin accumulation in potato tuber tissue. Plant Physiol. 1987 Jun;84(2):520-5. PubMed PMID: 16665472; PubMed Central PMCID: PMC1056613. 12: Alves LM, Heisler EG, Kissinger JC, Patterson JM, Kalan EB. Effects of Controlled Atmospheres on Production of Sesquiterpenoid Stress Metabolites by White Potato Tuber: Possible Involvement of Cyanide-resistant Respiration. Plant Physiol. 1979 Feb;63(2):359-62. PubMed PMID: 16660728; PubMed Central PMCID: PMC542829. 13: Komaraiah P, Reddy GV, Reddy PS, Raghavendra AS, Ramakrishna SV, Reddanna P. Enhanced production of antimicrobial sesquiterpenes and lipoxygenase metabolites in elicitor-treated hairy root cultures of Solanum tuberosum. Biotechnol Lett. 2003 Apr;25(8):593-7. PubMed PMID: 12882150. 14: Tugizimana F, Steenkamp PA, Piater LA, Dubery IA. Ergosterol-induced sesquiterpenoid synthesis in tobacco cells. Molecules. 2012 Feb 9;17(2):1698-715. doi: 10.3390/molecules17021698. PubMed PMID: 22322447. 15: Loser K, Weltring K. Induction of a polyubiquitin gene (ubi1) by potato phytoalexins and heat shock in Gibberella pulicaris. Curr Genet. 1998 Dec;34(5):404-9. PubMed PMID: 9871124. 16: Furze JM, Rhodes MJ, Parr AJ, Robins RJ, Withehead IM, Threlfall DR. Abiotic factors elicit sesquiterpenoid phytoalexin production but not alkaloid production in transformed root cultures of Datura stramonium. Plant Cell Rep. 1991 Jun;10(3):111-4. doi: 10.1007/BF00232039. PubMed PMID: 24221487. 17: Yokose T, Katamoto K, Park S, Matsuura H, Yoshihara T. Anti-fungal sesquiterpenoid from the root exudate of Solanum abutiloides. Biosci Biotechnol Biochem. 2004 Dec;68(12):2640-2. PubMed PMID: 15618642. 18: Tugizimana F, Steenkamp PA, Piater LA, Dubery IA. Multi-platform metabolomic analyses of ergosterol-induced dynamic changes in Nicotiana tabacum cells. PLoS One. 2014 Jan 31;9(1):e87846. doi: 10.1371/journal.pone.0087846. eCollection 2014. PubMed PMID: 24498209; PubMed Central PMCID: PMC3909234. 19: Fanelli C, Castoria R, Fabbri AA, Passi S. Novel study on the elicitation of hypersensitive response by polyunsaturated fatty acids in potato tuber. Nat Toxins. 1992;1(2):136-46. PubMed PMID: 1344908. 20: Fleissner A, Sopalla C, Weltring KM. An ATP-binding cassette multidrug-resistance transporter is necessary for tolerance of Gibberella pulicaris to phytoalexins and virulence on potato tubers. Mol Plant Microbe Interact. 2002 Feb;15(2):102-8. PubMed PMID: 11876422.

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