MedKoo Cat#: 461268 | Name: Reynosin

Description:

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

Reynosin is a sesquiterpene from the leaves of Laurus nobilis.

Chemical Structure

Reynosin
Reynosin
CAS#28254-53-7

Theoretical Analysis

MedKoo Cat#: 461268

Name: Reynosin

CAS#: 28254-53-7

Chemical Formula: C15H20O3

Exact Mass: 248.1412

Molecular Weight: 248.32

Elemental Analysis: C, 72.55; H, 8.12; O, 19.33

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
Reynosin;
IUPAC/Chemical Name
(3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a-methyl-3,9-dimethylenedecahydronaphtho[1,2-b]furan-2(3H)-one
InChi Key
FKBUODICGDOIGB-PFFFPCNUSA-N
InChi Code
InChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h10-13,16H,1-2,4-7H2,3H3/t10-,11+,12+,13-,15-/m0/s1
SMILES Code
O=C(O[C@@]1([H])[C@@]2([H])CC[C@@]3(C)[C@H](O)CCC([C@@]31[H])=C)C2=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
>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 248.32 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: Lim S, Lee SJ, Nam KW, Kim KH, Mar W. Hepatoprotective effects of reynosin against thioacetamide-induced apoptosis in primary hepatocytes and mouse liver. Arch Pharm Res. 2013 Apr;36(4):485-94. doi: 10.1007/s12272-013-0039-0. Epub 2013 Feb 24. PubMed PMID: 23435943. 2: Ham A, Kim DW, Kim KH, Lee SJ, Oh KB, Shin J, Mar W. Reynosin protects against neuronal toxicity in dopamine-induced SH-SY5Y cells and 6-hydroxydopamine-lesioned rats as models of Parkinson's disease: Reciprocal up-regulation of E6-AP and down-regulation of α-synuclein. Brain Res. 2013 Aug 2;1524:54-61. doi: 10.1016/j.brainres.2013.05.036. Epub 2013 Jun 8. PubMed PMID: 23751361. 3: Coronado-Aceves EW, Velázquez C, Robles-Zepeda RE, Jiménez-Estrada M, Hernández-Martínez J, Gálvez-Ruiz JC, Garibay-Escobar A. Reynosin and santamarine: two sesquiterpene lactones from Ambrosia confertiflora with bactericidal activity against clinical strains of Mycobacterium tuberculosis. Pharm Biol. 2016 Nov;54(11):2623-2628. Epub 2016 May 14. PubMed PMID: 27180996. 4: Jung JH, Ha JY, Min KR, Shibata F, Nakagawa H, Kang SS, Chang IM, Kim Y. Reynosin from Sassurea lappa as inhibitor on CINC-1 induction in LPS-stimulated NRK-52E cells. Planta Med. 1998 Jun;64(5):454-5. PubMed PMID: 9690347. 5: el-Feraly FS, Chan YM. Isolation and characterization of the sesquiterpene lactones costunolide, parthenolide, costunolide diepoxide, santamarine, and reynosin from Magnolia grandiflora L. J Pharm Sci. 1978 Mar;67(3):347-50. PubMed PMID: 641720. 6: Zhao XP, Lu L, Hu B, Wang SF. [Screening and identifying hepatotoxic components in Aucklandiae Radix with GC-MS]. Zhejiang Da Xue Xue Bao Yi Xue Ban. 2012 Jan;41(1):43-6. Chinese. PubMed PMID: 22419462. 7: Cho JY, Park J, Yoo ES, Baik KU, Jung JH, Lee J, Park MH. Inhibitory effect of sesquiterpene lactones from Saussurea lappa on tumor necrosis factor-alpha production in murine macrophage-like cells. Planta Med. 1998 Oct;64(7):594-7. PubMed PMID: 9810262. 8: Al-Attas AA, El-Shaer NS, Mohamed GA, Ibrahim SR, Esmat A. Anti-inflammatory sesquiterpenes from Costus speciosus rhizomes. J Ethnopharmacol. 2015 Dec 24;176:365-74. doi: 10.1016/j.jep.2015.11.026. Epub 2015 Nov 28. PubMed PMID: 26593213. 9: Wei H, He C, Peng Y, Ma G, Xiao P. [Chemical constituents of Dolomiaea souliei]. Zhongguo Zhong Yao Za Zhi. 2012 May;37(9):1249-53. Chinese. PubMed PMID: 22803370. 10: Choi JY, Choi EH, Jung HW, Oh JS, Lee WH, Lee JG, Son JK, Kim Y, Lee SH. Melanogenesis inhibitory compounds from Saussureae Radix. Arch Pharm Res. 2008 Mar;31(3):294-9. doi: 10.1007/s12272-001-1154-0. Epub 2008 Apr 13. PubMed PMID: 18409040. 11: Barrero AF, Oltra JE, Cuerva JM, Rosales A. Effects of solvents and water in Ti(III)-mediated radical cyclizations of epoxygermacrolides. Straightforward synthesis and absolute stereochemistry of (+)-3alpha-hydroxyreynosin and related eudesmanolides. J Org Chem. 2002 Apr 19;67(8):2566-71. PubMed PMID: 11950302. 12: Li S, An TY, Li J, Shen Q, Lou FC, Hu LH. PTP1B inhibitors from Saussrurea lappa. J Asian Nat Prod Res. 2006 Apr-May;8(3):281-6. PubMed PMID: 16864436. 13: Zhang T, Ma L, Wu F, Chen R. [Chemical constituents from a portion of ethanolicextract of Saussurea lappa roots]. Zhongguo Zhong Yao Za Zhi. 2012 May;37(9):1232-6. Chinese. PubMed PMID: 22803366. 14: Rivero A, Quintana J, Eiroa JL, López M, Triana J, Bermejo J, Estévez F. Potent induction of apoptosis by germacranolide sesquiterpene lactones on human myeloid leukemia cells. Eur J Pharmacol. 2003 Dec 15;482(1-3):77-84. PubMed PMID: 14660007. 15: Gören N, Woerdenbag HJ, Bozok-Johansson C. Cytotoxic and antibacterial activities of sesquiterpene lactones isolated from Tanacetum praeteritum subsp. praeteritum. Planta Med. 1996 Oct;62(5):419-22. PubMed PMID: 8923806. 16: De Marino S, Borbone N, Zollo F, Ianaro A, Di Meglio P, Iorizzi M. New sesquiterpene lactones from Laurus nobilis leaves as inhibitors of nitric oxide production. Planta Med. 2005 Aug;71(8):706-10. PubMed PMID: 16142632. 17: Hilmi F, Sticher O, Heilmann J. New cytotoxic sesquiterpene lactones from Warionia saharae. Planta Med. 2003 May;69(5):462-4. PubMed PMID: 12802731. 18: Wang BG, Hong X, Li L, Zhou J, Hao XJ. Chemical constituents of two Chinese Magnoliaceae plants, Tsoongiodendron odorum and Manglietiastrum sinicum, and their inhibition of platelet aggregation. Planta Med. 2000 Aug;66(6):511-5. PubMed PMID: 10985075. 19: Yoshikawa M, Shimoda H, Uemura T, Morikawa T, Kawahara Y, Matsuda H. Alcohol absorption inhibitors from bay leaf (Laurus nobilis): structure-requirements of sesquiterpenes for the activity. Bioorg Med Chem. 2000 Aug;8(8):2071-7. PubMed PMID: 11003152. 20: da Silva BP, Nepomuceno MP, Varela RM, Torres A, Molinillo JMG, Alves PLCA, Macías FA. Phytotoxicity Study on Bidens sulphurea Sch. Bip. as a Preliminary Approach for Weed Control. J Agric Food Chem. 2017 Jun 28;65(25):5161-5172. doi: 10.1021/acs.jafc.7b01922. Epub 2017 Jun 20. PubMed PMID: 28605187.