96990-18-0

Basic information

• Product Name: MOMORDINIC
• Synonyms: MorModin Ic;MOMORDINIC;28-norolean-12-en-3-yl 3-O-β-D-xylopyranosyl-;β-D-Glucopyranosiduronic acid, (3β)-17-carboxy-;Ic Momordin Ic;Momordin 1c;28-Noroleanane,β-D-glucopyranosiduronic acid deriv;Momordin IC, 98%, from Kochia scoparia(L.)Schrad.
• CAS NO: 96990-18-0
• Molecular Formula: C₄₁H₆₄O₁₃
• Molecular Weight: 764.944
• Product Categories: pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;chemical reagent
• Mol File: 96990-18-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 238-240 °C
• Boiling Point: 886.229 °C at 760 mmHg
• Flash Point: 263.092 °C
• Appearance: /
• Density: 1.35 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.605
• Storage Temp.: 2-8°C
• Solubility: Methanol (Slightly, Heated, Sonicated), Pyridine (Slightly)
• PKA: 2.75±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: MOMORDINIC(CAS DataBase Reference)
• NIST Chemistry Reference: MOMORDINIC(96990-18-0)
• EPA Substance Registry System: MOMORDINIC(96990-18-0)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 96990-18-0(Hazardous Substances Data)

Usage

Uses

Mormodin Ic is used as an anti-cancer agent, and is shown to induce HepG2 apoptosis in a PI3K and MAPK pathway-dependant manner.

InChI:InChI=1/C41H64O13/c1-36(2)14-16-41(35(49)50)17-15-39(6)20(21(41)18-36)8-9-24-38(5)12-11-25(37(3,4)23(38)10-13-40(24,39)7)52-34-29(46)30(28(45)31(54-34)32(47)48)53-33-27(44)26(43)22(42)19-51-33/h8,21-31,33-34,42-46H,9-19H2,1-7H3,(H,47,48)(H,49,50)/t21-,22+,23-,24+,25-,26-,27+,28-,29+,30-,31-,33-,34+,38-,39+,40+,41-/m0/s1

Synthetic route

3-O-[β-D-glucopyranosyl-(1-2)-(β-D-xylopyranosyl-(1-3))-β-D-glucuronopyranosyl]-3β-hydroxyolean-12-en-28-oic acid → (3β)-17-carboxy-28-norolean-12-en-3-yl 3'-O-(β-D-xylopyranosyl)-β-D-glucuronide (96990-18-0) + calenduloside E (26020-14-4, 108322-31-2) + zingibroside R1

Conditions	Yield
With sulfuric acid at 80℃; for 10h;	A 14 mg B 31 mg C 23 mg

(3β)-17-carboxy-28-norolean-12-en-3-yl 3'-O-(β-D-xylopyranosyl)-β-D-glucuronide (96990-18-0) → calenduloside E (26020-14-4, 108322-31-2)

Conditions	Yield
With hydrogenchloride	32 mg

(3β)-17-carboxy-28-norolean-12-en-3-yl 3'-O-(β-D-xylopyranosyl)-β-D-glucuronide (96990-18-0) → Oleanolic acid (508-02-1) + calenduloside E (26020-14-4, 108322-31-2)

Conditions	Yield
With sulfuric acid at 80℃; for 10h;	A n/a B 34 mg

methanol (67-56-1) + (3β)-17-carboxy-28-norolean-12-en-3-yl 3'-O-(β-D-xylopyranosyl)-β-D-glucuronide (96990-18-0) → momordin Ic 6'-methyl ester

Conditions	Yield
With hydrogenchloride for 2.5h; Heating;	26 mg

(3β)-17-carboxy-28-norolean-12-en-3-yl 3'-O-(β-D-xylopyranosyl)-β-D-glucuronide (96990-18-0) → oleanolic acid 3-O-β-D-xylopyranosyl-(1->3)-β-D-glucopyranoside

Conditions	Yield
Multi-step reaction with 2 steps 1: 26 mg / 3 percent HCl / 2.5 h / Heating 2: 45 mg / NaBH4 / methanol / 1 h / Ambient temperature View Scheme

Upstream product

• 67-56-1 methanol 
• 129385-80-4 Hemsloside G₁ 

Downstream Products

• 508-02-1 Oleanolic acid 
• 26020-14-4 calenduloside E 

Relevant articles and documents

Triterpenoid glycosides from the fruits of Kochia scoparia

From the fruits of Kochia scoparia (L.) Schrad, five triterpenoid glycosides were isolated for the first time from this plant. They were elucidated as momordin 1c, the 6'-methyl ester of momordin 1c, momordin IIc, 2'-O-β-D-glucopyranosylmomordin Ic, and 2'-O-β-D-glucopyranosylmomordin IIc on the basis of spectral and chemical methods. The last two saponins are new natural products.