Sarmentosine

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

MedKoo CAT#: 461819

CAS#: 71933-54-5

Description: 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

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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 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 @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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

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

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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.