MedKoo Cat#: 461819 | Name: Sarmentosine

Description:

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

Sarmentosine is a member of the class of compounds known as fatty acyl glycosides of mono- and disaccharides and is isolated from Ribes nigrum.

Chemical Structure

Sarmentosine
Sarmentosine
CAS#71933-54-5

Theoretical Analysis

MedKoo Cat#: 461819

Name: Sarmentosine

CAS#: 71933-54-5

Chemical Formula: C11H17NO7

Exact Mass: 275.1005

Molecular Weight: 275.25

Elemental Analysis: C, 48.00; H, 6.23; N, 5.09; O, 40.69

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
Sarmentosine;
IUPAC/Chemical Name
(E)-2-(hydroxymethyl)-4-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)but-2-enenitrile
InChi Key
FWAYDNJCBHNWQD-JBWLPIRVSA-N
InChi Code
InChI=1S/C11H17NO7/c12-3-6(4-13)1-2-18-11-10(17)9(16)8(15)7(5-14)19-11/h1,7-11,13-17H,2,4-5H2/b6-1+/t7-,8-,9+,10-,11-/m1/s1
SMILES Code
N#C/C(CO)=C\CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
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 275.25 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: Hussain K, Ismail Z, Sadikun A, Ibrahim P. Bioactive Markers Based Pharmacokinetic Evaluation of Extracts of a Traditional Medicinal Plant, Piper sarmentosum. Evid Based Complement Alternat Med. 2011;2011:980760. doi: 10.1093/ecam/nep143. Epub 2011 Jun 23. PubMed PMID: 19770264; PubMed Central PMCID: PMC3137875. 2: Hussain K, Ismail Z, Sadikun A, Ibrahim P. Standardization and in vivo antioxidant activity of ethanol extracts of fruit and leaf of Piper sarmentosum. Planta Med. 2010 Mar;76(5):418-25. doi: 10.1055/s-0029-1186279. Epub 2009 Oct 27. PubMed PMID: 19862670. 3: Tuntiwachwuttikul P, Phansa P, Pootaeng-On Y, Taylor WC. Chemical constituents of the roots of Piper sarmentosum. Chem Pharm Bull (Tokyo). 2006 Feb;54(2):149-51. PubMed PMID: 16462055. 4: Khalid H, Zhari I, Amirin S, Pazilah I. Accelerated Stability and Chemical Kinetics of Ethanol Extracts of Fruit of Piper sarmentosum Using High Performance Liquid Chromatography. Iran J Pharm Res. 2011 Summer;10(3):403-13. PubMed PMID: 24250372; PubMed Central PMCID: PMC3813043. 5: Bjarnholt N, Nakonieczny M, Kędziorski A, Debinski DM, Matter SF, Olsen CE, Zagrobelny M. Occurrence of sarmentosin and other hydroxynitrile glucosides in Parnassius (papilionidae) butterflies and their food plants. J Chem Ecol. 2012 May;38(5):525-37. doi: 10.1007/s10886-012-0114-x. Epub 2012 Apr 25. PubMed PMID: 22527055. 6: Zhang H, Xu R, Hu Z, He X, Bai D, Li X, Wang X. Synthesis of aglycon analogues of sarmentosin and their bioactivity of lymphocyte proliferation. Bioorg Med Chem Lett. 2002 Dec 16;12(24):3543-5. PubMed PMID: 12443772. 7: Shen ML, Zhai SK, Lu ZW, Ou DW. Two simple glucose derivatives with opposite immunoactivities. Ann N Y Acad Sci. 1993 Jun 23;685:377-82. PubMed PMID: 8363245. 8: Lian LH, Jin X, Wu YL, Cai XF, Lee JJ, Nan JX. Hepatoprotective effects of Sedum sarmentosum on D-galactosamine/lipopolysaccharide-induced murine fulminant hepatic failure. J Pharmacol Sci. 2010;114(2):147-57. Epub 2010 Sep 11. PubMed PMID: 20838028. 9: Rukachaisirikul T, Siriwattanakit P, Sukcharoenphol K, Wongvein C, Ruttanaweang P, Wongwattanavuch P, Suksamrarn A. Chemical constituents and bioactivity of Piper sarmentosum. J Ethnopharmacol. 2004 Aug;93(2-3):173-6. PubMed PMID: 15234750.