17184-21-3

Basic information

• Product Name: cauloside A
• Synonyms: cauloside A;3β-(α-L-Arabinopyranosyloxy)-23-hydroxy-5α-olean-12-en-28-oic acid;3β-(α-L-Arabinopyranosyloxy)-23-hydroxyolean-12-en-28-oic acid;Hederagenin 3-O-α-L-arabinoside;Prosapogenin CP1;3-(α-L-Arabinopyranosyloxy)-23-hydroxyoleana-12-ene-28-oic acid;Hederaginin 3-O-α-L-arabinopyranoside;beta2-Fatsin
• CAS NO: 17184-21-3
• Molecular Formula: C35H56O8
• Molecular Weight: 604.81434
• Mol File: 17184-21-3.mol
• Article Data: 27

Chemical Properties

• Melting Point: 276-278℃
• Boiling Point: 719.3°C at 760 mmHg
• Flash Point: 219.7°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 6.76E-24mmHg at 25°C
• Refractive Index: 1.589
• PKA: 4.63±0.70(Predicted)
• CAS DataBase Reference: cauloside A(CAS DataBase Reference)
• NIST Chemistry Reference: cauloside A(17184-21-3)
• EPA Substance Registry System: cauloside A(17184-21-3)

Safety Data

• Hazardous Substances Data: 17184-21-3(Hazardous Substances Data)

Usage

Definition

ChEBI: A triterpenoid saponin that is hederagenin attached to an alpha-L-arabinopyranosyl residue at position 3 via a glycosidic linkage.

InChI:InChI=1/C35H56O8/c1-30(2)13-15-35(29(40)41)16-14-33(5)20(21(35)17-30)7-8-24-31(3)11-10-25(43-28-27(39)26(38)22(37)18-42-28)32(4,19-36)23(31)9-12-34(24,33)6/h7,21-28,36-39H,8-19H2,1-6H3,(H,40,41)/t21-,22-,23+,24+,25-,26-,27+,28-,31-,32-,33+,34+,35-/m0/s1

Upstream product

• 186581-53-3 diazomethane 
• 14216-03-6 HN-saponin P 
• 39524-08-8 3-O-<α-L-arabinopyranosyl>hederagenin 28-O-<β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside> 
• 38631-44-6 hederagenin 3-O-<β-D-xylopyranosyl-(1-2)-α-L-arabinopyranoside> 
• 20853-58-1 hederagenin 3-O-β-D-glucopyranosyl-(1->2)-O-α-L-arabinopyranoside 
• 39524-13-5 3β-[(α-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranosyl ester 
• 12672-45-6 cauloside D 
• 27013-91-8 alpha-Hederin 
• 119742-55-1 hederagenin-3-O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester 
• 29781-27-9 hederagenin 3-O-β-D-glucopyranosyl-(1-4)-β-D-xylopyranosyl-(1-3)-α-L-rhamnopyranosyl-(1-2)-α-L-arabinopyranoside 
• 29781-27-9 C₅₂H₈₄O₂₁ 
• 495-76-1 piperonol 
• 120-57-0 piperonal 
• 4299-70-1 D-Tryptophan methyl ester 

Downstream Products

• 87-72-9 L-(+)-arabinose 
• 465-99-6 hedaragenin 
• 7296-55-1 L-arabinose 

Relevant articles and documents

A TRITERPENOID SAPONIN FROM FICARIA RANUNCULOIDES TUBERS

One of the minor saponins extracted from the tubers of Ficaria ranunculoides and purified by fermentation may be 3-O-(α-arabinopyranosyl-1')28-O-6''(α-rhamnopyranosyl-1'''->4'')β-glucopyranosyl-1''>-hederagenin.On the basis of chemical degradation and spectral analysis, the structure of this new saponin is proposed. Key Word Index - Ficaria ranunculoides; Ranunculaceae; triterpenoid saponin; 3-O-(α-arabinopyranosyl-1')28-O-6''(α-rhamnopyranosyl-1'''->4'')β-glucopyranosyl 1''>-hederagenin.

Antibacterial activity of a triterpenoid saponin from the stems of Caesalpinia pulcherrima Linn.

A new compound 1 was isolated from the methanolic extract of the stems of the Caesalpinia pulcherrima Linn. along with a reported compound (2) 3-O-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester. The new compound 1 has m.p. 272–274°C, m.f. C46H74O17, [M]+ m/z 898. It was characterised as 3-O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl hederagenin 28-O-β-D- xylopyranosyl ester by various colour reactions, chemical degradations and spectral analyses. Antibacterial activity of compound 1 was screened against various Gram-positive and Gram-negative bacteria and showed significant results.

Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis

Investigation of the n-BuOH extract of the rhizomes of Anemone taipaiensis led to the isolation of five new oleanane-type triterpenoid saponins (1-5), together with seven known saponins (6-12). Their structures were determined by the extensive use of 1D and 2D NMR experiments along with ESIMS analyses and acid hydrolysis. The aglycone of 1, 2 and 4 was determined as siaresinolic acid, which was reported in this genus for the first time. The cytotoxicities of the saponins 1-12, prosapogenins 4a, 5a, 10a-12a and sapogenins siaresinolic acid (SA), oleanolic acid (OA), hederagenin (HE) were evaluated against five human cancer cell lines, including HepG2, HL-60, A549, HeLa and U87MG. The monodesmosidic saponins 6-8, 5a, 10a-12a and sapogenins SA, OA, HE exhibited cytotoxic activity toward all cancer cell lines, with IC 50 values ranging from 2.25 to 57.28 μM. Remarkably, the bisdesmosidic saponins 1-4 and 9 showed selective cytotoxicity against the U87MG cells.