Teupolioside | CAS#143617-02-1 | putatively ameliorates colitis

MedKoo Cat#: 598253 | Name: Teupolioside

Description:

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

Teupolioside is a putatively ameliorates colitis; isolated from Ajuga reptans.

Chemical Structure

Teupolioside

CAS#143617-02-1

Theoretical Analysis

MedKoo Cat#: 598253

Name: Teupolioside

CAS#: 143617-02-1

Chemical Formula: C35H46O20

Exact Mass: 786.2582

Molecular Weight: 786.73

Elemental Analysis: C, 53.43; H, 5.89; O, 40.67

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

Teupolioside; Lamiuside A; Teupolioside HTN; trans-Lamalboside;

IUPAC/Chemical Name

(2R,3R,4R,5R,6R)-4-(((2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6-(3,4-dihydroxyphenethoxy)-5-hydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl (E)-3-(3,4-dihydroxyphenyl)acrylate

InChi Key

SDRRSTAVRUERNC-GUTOYVNHSA-N

InChi Code

InChI=1S/C35H46O20/c1-14-24(43)27(46)32(55-34-28(47)26(45)25(44)21(12-36)51-34)35(50-14)54-31-29(48)33(49-9-8-16-3-6-18(39)20(41)11-16)52-22(13-37)30(31)53-23(42)7-4-15-2-5-17(38)19(40)10-15/h2-7,10-11,14,21-22,24-41,43-48H,8-9,12-13H2,1H3/b7-4+/t14-,21+,22+,24-,25-,26-,27+,28+,29+,30+,31+,32+,33+,34-,35-/m0/s1

SMILES Code

C[C@H]1[C@H](O)[C@@H](O)[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O2)[C@H](O[C@@H]3[C@@H](O)[C@H](OCCc4cc(O)c(O)cc4)O[C@H](CO)[C@H]3OC(/C=C/c5cc(O)c(O)cc5)=O)O1

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 786.73 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.

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: Di Paola R, Esposito E, Mazzon E, Riccardi L, Caminiti R, Dal Toso R, Pressi G, Cuzzocrea S. Teupolioside, a phenylpropanoid glycosides of Ajuga reptans, biotechnologically produced by IRBN22 plant cell line, exerts beneficial effects on a rodent model of colitis. Biochem Pharmacol. 2009 Mar 1;77(5):845-57. doi: 10.1016/j.bcp.2008.11.010. Epub 2008 Nov 25. PubMed PMID: 19070602. 2: Pastore S, Potapovich A, Kostyuk V, Mariani V, Lulli D, De Luca C, Korkina L. Plant polyphenols effectively protect HaCaT cells from ultraviolet C-triggered necrosis and suppress inflammatory chemokine expression. Ann N Y Acad Sci. 2009 Aug;1171:305-13. doi: 10.1111/j.1749-6632.2009.04684.x. PubMed PMID: 19723070. 3: Prescott TA, Veitch NC, Simmonds MS. Direct inhibition of calcineurin by caffeoyl phenylethanoid glycosides from Teucrium chamaedrys and Nepeta cataria. J Ethnopharmacol. 2011 Oct 11;137(3):1306-10. doi: 10.1016/j.jep.2011.07.063. Epub 2011 Aug 6. PubMed PMID: 21843624. 4: Korkina LG, Mikhal'chik E, Suprun MV, Pastore S, Dal Toso R. Molecular mechanisms underlying wound healing and anti-inflammatory properties of naturally occurring biotechnologically produced phenylpropanoid glycosides. Cell Mol Biol (Noisy-le-grand). 2007 May 30;53(5):84-91. PubMed PMID: 17543237.