60976-49-0

Basic information

• Product Name: B-D-GLUCOPYRANOSE
• Synonyms: GERANIIN;B-D-GLUCOPYRANOSE;beta-D-Glucopyranose cyclic 2-7:4-5-(3,6-dihydro-2,9,10,11,11-pentahydroxy-3-oxo-2,6-methano-2H-1-benzoxocin-5,7-dicarboxylate) cyclic 3,6-(4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate) 1-(3,4,5-trihydroxybenzoate) stereoisomer;eraniin;5-(3,6-dihydro-2,9,10,11,11-pentahydroxy-3-oxo-2,6-Methano-2H-1-benzoxocin-5,7-dicarboxylate)cyclic 3,6-(4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate)1-(3,4,5-trihydroxybenzoate), stereoisoMer;7:4®b-D-Glucopyranose, cyclic 2®
• CAS NO: 60976-49-0
• Molecular Formula: C₄₁H₂₈O₂₇
• Molecular Weight: 180.15588
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 60976-49-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 2.25
• Refractive Index: 1.947
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 6.35±0.70(Predicted)
• CAS DataBase Reference: B-D-GLUCOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: B-D-GLUCOPYRANOSE(60976-49-0)
• EPA Substance Registry System: B-D-GLUCOPYRANOSE(60976-49-0)

Safety Data

• Hazardous Substances Data: 60976-49-0(Hazardous Substances Data)

Usage

Description

Geraniin is a tannin that has been found in P. urinaria and has diverse biological activities. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; IC50s = 0.92 and 1.27 μM at pH 4.5 and 7.9, respectively), superoxide (IC50 = 2.65 μM), and hydroxyl radicals (IC50 = 1.44 μM) in cell-free assays. Geraniin inhibits herpes simplex virus 1 (HSV-1) and HSV-2 replication in plaque reduction assays (IC50s = 35 and 18.4 μM, respectively). It inhibits angiotensin-converting enzyme (ACE) in vitro (IC50 = 13.22 μM) and reduces both systolic and diastolic blood pressure in spontaneously hypertensive rats when administered at a dose of 5 mg/kg. Geraniin (5, 10, and 20 μM) induces apoptosis and halts the cell cycle at the S phase in A549 lung cancer cells. It reduces tumor growth in an A549 mouse xenograft model when administered at doses of 10 and 20 mg/kg.

Uses

Geraniin protects PC12 cells against neuronal damage and may be used in the treatment of Alzheimer’s disease/ Also is an ACE inhibitor which is useful for hypertension treatment.

InChI:InChI=1/C41H28O27/c42-13-1-8(2-14(43)24(13)48)34(54)67-39-33-32-30(64-38(58)12-6-19(47)41(61)40(59,60)23(12)22-11(37(57)66-33)5-17(46)27(51)31(22)68-41)18(63-39)7-62-35(55)9-3-15(44)25(49)28(52)20(9)21-10(36(56)65-32)4-16(45)26(50)29(21)53/h1-6,18,23,30,32-33,39,42-46,48-53,59-61H,7H2

Synthetic route

ascorgeraniin (102382-31-0) → geraniin (81905-83-1) + geraniin (60976-49-0)

Conditions	Yield
In water at 37℃; for 18h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

ascorgeraniin (102382-31-0) → geraniin (60976-49-0) + geraniin (81905-83-1)

Conditions	Yield
In water at 90℃; for 1h; Heating; Yield given;

C46H34O32 → geraniin (60976-49-0) + ascorbic acid (50-81-7)

Conditions	Yield
for 3h; oxidative metabolizm; enzyme from fresh leaves and stems of Geranium thunbergii;

geraniin (60976-49-0) + 2-hydroxyethanethiol (60-24-2) → C43H34O28S

Conditions	Yield
In methanol at 20℃; for 36h; acetate buffer pH 4.0;	54%

geraniin (60976-49-0) → 1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-2,4-tetrahydroxydibenzofurandicarboxyl-β-D-glucose (124854-04-2) + 1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-4-O-brevifolincarboxyl-β-D-glucopyranose (132185-49-0) + 1-O-galloyl-2,4;3,6-bis-(R)-4,5,6,4,5,6-hexahydroxydiphenoyl-β-D-glucose (100227-56-3) + corilagin (23094-69-1)

Conditions	Yield
With pyridine In acetonitrile at 80℃; for 1.5h;	A 35.4% B 4% C 1.7% D 5%

GLUTATHIONE (70-18-8) + geraniin (60976-49-0) → C51H45N3O33S + C51H47N3O34S + C41H28O27 + C42H30O27

Conditions	Yield
at 22 - 27℃; for 8h; 0.1 M potassium-sodium phosphate buffer pH 7.0; Further byproducts given;	A 30% B 8% C 29% D 10%

GLUTATHIONE (70-18-8) + geraniin (60976-49-0) → C51H45N3O33S + C41H28O27 + C42H30O27 + corilagin (23094-69-1)

Conditions	Yield
at 22 - 27℃; for 8h; 0.1 M potassium-sodium phosphate buffer pH 7.0; Further byproducts given;	A 30% B 29% C 10% D 16%

N-acetylcystein (616-91-1) + geraniin (60976-49-0) → C51H44N2O32S2 + C41H28O27 + C46H37NO30S + C46H39NO31S

Conditions	Yield
at 25℃; for 8h; potassium-sodium phosphate buffer, pH 6.5; Further byproducts given;	A 10% B 6% C 20% D 7%

geraniin (60976-49-0) → 1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-4-O-brevifolincarboxyl-β-D-glucopyranose (132185-49-0) + repandusinic acid A (125516-10-1) + corilagin (23094-69-1)

Conditions	Yield
With sodium hydroxide at 70℃; for 0.0833333h;	A 12% B 17% C 17%

geraniin (60976-49-0) → C40H28O25 + 1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-4-O-brevifolincarboxyl-β-D-glucopyranose (132185-49-0)

Conditions	Yield
With sodium benzenesulfonate In acetonitrile at 80℃; for 3h;	A 12% B 3%

geraniin (60976-49-0) → 3,6-(R)-hexahydroxydiphenyl-(α/β)-glucopyranose + corilagin (23094-69-1)

Conditions	Yield
With water at 90℃; for 30h;	A n/a B 10%

geraniin (60976-49-0) → 1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-4-O-brevifolincarboxyl-β-D-glucopyranose (132185-49-0) + corilagin (23094-69-1)

Conditions	Yield
With triethylamine In acetonitrile at 80℃; for 0.166667h;	A 167 mg B 53 mg
With triethylamine In acetonitrile at 80℃; for 0.166667h; Product distribution; Mechanism; other bases, other dehydrohexahydroxydiphenic acid esters, other reaction times, other solvent;

geraniin (60976-49-0) + acetone (67-64-1) → Phyllanthusiin D (133145-19-4, 142035-50-5)

Conditions	Yield
With trifluoroacetic acid for 1h; Heating;	10 mg

geraniin (60976-49-0) + isoascorbic acid (89-65-6) → ascorgeraniin (102382-31-0)

Conditions	Yield
In methanol; water at 37℃; for 15h;

geraniin (60976-49-0) → 1-O-galloyl-2,4;3,6-bis-(R)-4,5,6,4,5,6-hexahydroxydiphenoyl-β-D-glucose (100227-56-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol for 24h;	0.54 g

geraniin (60976-49-0) → C49H36N2O25S

Conditions	Yield
Multi-step reaction with 2 steps 1: 54 percent / methanol / 36 h / 20 °C / acetate buffer pH 4.0 2: 27 percent / 10percent AcOH / methanol / 15 h / 20 °C View Scheme

geraniin (60976-49-0) → 3,6-(R)-hexahydroxydiphenyl-(α/β)-glucopyranose

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.54 g / H2 / Pd/C / ethanol / 24 h 2: H2O / 90 °C View Scheme

geraniin (60976-49-0) → corilagin (23094-69-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.54 g / H2 / Pd/C / ethanol / 24 h 2: 80 percent / H2O / 90 °C View Scheme
Multi-step reaction with 2 steps 1: 3 percent / sodium benzenesulfinate / acetonitrile / 3 h / 80 °C 2: 12 mg / 5percent HCl / 0.83 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: 167 mg / triethylamine / acetonitrile / 0.17 h / 80 °C 2: 12 mg / 5percent HCl / 0.83 h / 100 °C View Scheme

geraniin (60976-49-0) → brevifolin carboxylic acid (18482-98-9, 18486-19-6, 18490-95-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 3 percent / sodium benzenesulfinate / acetonitrile / 3 h / 80 °C 2: 7 mg / 5percent HCl / 0.83 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: 167 mg / triethylamine / acetonitrile / 0.17 h / 80 °C 2: 7 mg / 5percent HCl / 0.83 h / 100 °C View Scheme

geraniin (60976-49-0) → repandusinic acid A + corilagin (23094-69-1)

Conditions	Yield
In aq. phosphate buffer at 40℃; for 16h; pH=7.4;	A 6.3 mg B 14.9 mg

geraniin (60976-49-0) → ellagic acid (476-66-4)

Conditions	Yield
In aq. buffer at 22℃; pH=10; Kinetics; pH-value; Time;

Upstream product

• 102382-31-0 elaeocarpusin 

Downstream Products

• 1707-75-1 2,2-diphenyl-1-picrylhydrazine 
• 133145-19-4 Phyllanthusiin D 
• 476-66-4 ellagic acid 
• 23094-69-1 corilagin 
• 18482-98-9 brevifolin carboxylic acid 
• 100227-56-3 1-O-galloyl-2,4;3,6-bis-(R)-4,5,6,4,5,6-hexahydroxydiphenoyl-β-D-glucose 
• 102382-31-0 elaeocarpusin 
• 77259-46-2 C₄₇H₃₀N₂O₂₄ 
• 66108-78-9 geraniin-phenazine B 
• 132185-49-0 1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-4-O-brevifolincarboxyl-β-D-glucopyranose 
• 125516-10-1 repandusinic acid A 
• 124854-04-2 1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-2,4-tetrahydroxydibenzofurandicarboxyl-β-D-glucose 

Relevant articles and documents

Tannins and related compounds. XCIV. Isolation and characterization of seven new hydrolyzable tannins from the leaves of Macaranga tanarius (L.) Muell. et Arg.

-

Tannins and Related Compounds. Part 37.1 Isolation and Structure Elucidation of Elaeocarpusin, a Novel Ellagitannin from Elaeocarpus sylvestris var. Ellipticus

A new hydrolysable tannin, elaeocarpusin, isolated from the leaves of Elaeocarpus sylvestris var.Ellipticus, has been characterized on the basis of chemical, spectroscopic, and X-ray analyses to be a novel ellagitannin in which a unique acid ester group probably derived by a condensation of a hexahydroxydiphenoyl group and dehydroascorbic acid is attached to the 2,4-positions of 1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-D-glucopyranose (corilagin).This structural feature suggest the possibility of the participation of dehydroascorbic acid as a co-enzyme in oxidative metabolism of the hexahydroxydiphenoyl group to the corresponding dehydro group.