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153-18-4

Basic Information
CAS No.: 153-18-4
Name: Rutin
Article Data: 9
Cas Database
Molecular Structure:
Molecular Structure of 153-18-4 (Rutin)
Formula: C27H30O16
Molecular Weight: 610.526
Synonyms: Forsythia fruit;Birutin;Oxyritin;4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-;Venoruton;Rutinion acid;Tanrutin;C.I. 75730;Rutinic acid;Rutoside;
EINECS: 205-814-1
Density: 1.827 g/cm3
Melting Point: 195 °C (dec.)(lit.)
Boiling Point: 983.1 °C at 760 mmHg
Flash Point: 325.4 °C
Solubility: 12.5 g/100 mL in water
Appearance: pale-yellow crystalline solid
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-36/37/38
Safety: 24/25-36-26
Transport Information: N/A
PSA: 269.43000
LogP: -1.68710
Synthetic route

A

B

100-22-1

N,N,N',N'-tetramethyl-para-phenylenediamine

rutin radical

rutin radical

A

N,N,N',N'-tetramethyl-para-semiquinonediimine
100-22-1

N,N,N',N'-tetramethyl-para-semiquinonediimine

B

153-18-4

rutin

Conditions
ConditionsYield
at 20℃; Equilibrium constant; pH=13.5;
at 20℃; Rate constant; Equilibrium constant; pH=13.5;
potassium-compound of quercetin

potassium-compound of quercetin

Conditions
ConditionsYield
With α-acetobromorutinose in fluessigem NH3;

A

482-35-9

isoquercetin

B

117-39-5

quercetol

C

153-18-4

rutin

Conditions
ConditionsYield
With ammonium bicarbonate In acetic acid methyl ester; water at 45℃; for 0.75h; Purification / work up;
In acetic acid methyl ester; water at 45℃; for 0.5h; Purification / work up;

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-O-{6-deoxy-2-O-[(4-hydroxy-3,5-dimethoxyphenyl)carbonyl]-α-L-mannopyranosyl}-β-D-glucopyranoside

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 1h;

482-35-9

isoquercetin

Conditions
ConditionsYield
With Aspergillus niger crude enzyme extract In methanol at 60℃; for 4h; pH=6; aq. piperazine-HCl buffer; Enzymatic reaction;99%
With hesperidinase In aq. buffer at 40℃; for 0.666667h; pH=9; Activation energy; Temperature; Concentration; Ionic liquid; Enzymatic reaction;98.6%
With hesperidinase from Aspergillus niger; water In aq. buffer at 40℃; for 0.666667h; pH=9; Temperature; Flow reactor; Enzymatic reaction;98.6%

rutin 2'',2''',3',3'',3''',4',4'',4''',5, 7-O-decasulfate

Conditions
ConditionsYield
Stage #1: rutin With triethylamine sulfurtrioxide In N,N-dimethyl acetamide at 20 - 100℃; for 0.5h; Microwave irradiation;
Stage #2: With triethylamine In N,N-dimethyl acetamide; acetone at 4℃; for 24h;
Stage #3: With sodium acetate In water
99%

Conditions
ConditionsYield
With hydrogenchloride; methanol for 3h; Heating;96%
With water at 100℃; Kinetics; Ionic liquid;90%
With sulfuric acid; water at 20℃; for 0.166667h;89%

rutin

rutin

7085-55-4

troxerutin

Conditions
ConditionsYield
With chitosan In methanol at 75℃; for 3h; Concentration; Temperature; Autoclave;96%
With natural polymer sodium alginate In methanol at 70℃; for 4h; Temperature; Autoclave;87.6%
Stage #1: oxirane; rutin With sodium hydroxide In water at 75℃; for 6h;
Stage #2: With hydrogenchloride In water pH=4;
isoquercitrin

isoquercitrin

Conditions
ConditionsYield
With α-L-rhamnosidase from Aspergillus niger JMU-TS528 at 60℃; for 1h; pH=3 - 5; Kinetics; Catalytic behavior; pH-value; Temperature; Concentration; Enzymatic reaction;95.1%
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Specification

Rutin, its cas register number is 153-18-4. The other name is rutoside, quercetin-3-rutinoside and sophorin and it is a citrus flavonoid glycoside found in buckwheat, the leaves and asparagus, and petioles of Rheum species. Rutin is also found in the fruit of the Fava D'Anta tree, fruits and fruit rinds and berries such as mulberry and cranberries. Its name comes from the name of Ruta graveolens, a plant that also contains rutin.

Physical properties about Rutin are: (1)ACD/LogP: -0.903; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): -0.99; (4)ACD/LogD (pH 7.4): -2.44; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4):1.00; (7)ACD/KOC (pH 5.5): 6.32 ; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 16; (10)#H bond donors: 10; (11)#Freely Rotating Bonds: 16; (12)Index of Refraction: 1.765; (13)Molar Refractivity: 138.172 cm3; (14)Molar Volume: 334.168 cm3; (15)Polarizability: 54.776 10-24cm3; (16)Surface Tension: 125.226997375488 dyne/cm; (17)Density: 1.827 g/cm3; (18)Flash Point: 325.407 °C; (19)Enthalpy of Vaporization: 150.124 kJ/mol; (20)Boiling Point: 983.144 °C at 760 mmHg

When you are using Rutin, please be cautious about it as the following:
1. Avoid contact with skin and eyes;

2. Wear suitable protective clothing;
3. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1;
(2)InChIKey=IKGXIBQEEMLURG-NVPNHPEKSA-N;
(3)Smilesc1(c(c(c2c(cc(cc2o1)O)O)=O)O[C@@H]1O[C@H](CO[C@H]2[C@@H]([C@@H]([C@@H](O)[C@@H](O2)C)O)O)[C@@H](O)[C@@H]([C@H]1O)O)c1cc(c(O)cc1)O

 The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intraperitoneal 2gm/kg (2000mg/kg)   Eksperimentalna Meditsina i Morfologiya. Vol. 19, Pg. 207, 1980.
mouse LD50 intraperitoneal 200mg/kg (200mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 intravenous 950mg/kg (950mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 39, Pg. 556, 1950.
rat LD50 intraperitoneal 2gm/kg (2000mg/kg)   Eksperimentalna Meditsina i Morfologiya. Vol. 19, Pg. 207, 1980.

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