119170-52-4 Usage
Description
Cassiaside C belongs to the class of organic compounds known as naphthopyranone glycosides. Naphthopyranone glycosides are compounds containing a carbohydrate moiety glycosidically linked to a naphthopyranone moiety. Cassiaside C has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, herbs and spices, pulses, and robusta coffees (Coffea canephora). This could make cassiaside C a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cassiaside C.
Synthesis
1.Add Ag2CO3 (414 mg, 1.50 mmol) to a stirring suspension of 2,3,4-tri-O-benzoyl-6-O-acetyl-D-glucopyranosyl bromide (6d, 596 mg, 1.00 mmol) in acetone (10 mL) and water (0.5 mL) portionwise.2.After stirring for 40 minutes at ambient temperature, filter the mixture through a pad of Celite.3.Wash the filtrate with acetone.4.Dry the filtrate.5.Concentrate the filtrate.6.Purify the residue by column chromatography (petroleum ether-EtOAc, 3:1).
in vitro
Cassiaside C is a naphthopyrone isolated from the seed of Cassia tora. It has inhibitory activity on advanced glycation end products (AGE) formation in vitro.
Check Digit Verification of cas no
The CAS Registry Mumber 119170-52-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,9,1,7 and 0 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 119170-52:
(8*1)+(7*1)+(6*9)+(5*1)+(4*7)+(3*0)+(2*5)+(1*2)=114
114 % 10 = 4
So 119170-52-4 is a valid CAS Registry Number.
119170-52-4Relevant articles and documents
Total synthesis of the antiallergic naphtho-α-pyrone tetraglucoside, cassiaside C2, isolated from Cassia seeds
Zhang, Zhaojun,Yu, Biao
, p. 6309 - 6313 (2007/10/03)
Toralactone 9-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-(1→3)- P-D-glucopyranosyl-(1-6)-β-D-glucopyranoside (1, cassiaside C2), isolated from Cassia obtusifolia L. and showing strong antiallergic activity, was concisely synthesized employing glycosyl trifluoroacetimidates as glycosylation agents. The unique naphtho-α-pyrone structure of toralactone (5) was constructed by condensation of orsellinate 8 with pyrone 9 in the presence of LDA as developed by Staunton and co-workers. The naphthol of toralactone showed minimal reactivity as an acceptor and was screened with various glycosyl donors. It is finally concluded that sacrifice of an excess amount of the trifluoroacetimidate or trichloroacetimidate donors (6f/6g, 6.0 equiv) in the presence of a catalytic amount of TMSOTf (0.05 and 0.3 equiv, respectively) afforded excellent yields of the coupling product, which was otherwise only a minor product under a variety of conditions examined.
