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153-18-4

Basic Information
CAS No.: 153-18-4
Name: Rutin
Molecular Structure:
Molecular Structure of 153-18-4 (Rutin)
Formula: C27H30O16
Molecular Weight: 610.52
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:
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%
108-30-5

succinic acid anhydride

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{{2,3,4-tris-O-(3-carboxy-1-oxopropyl)-6-O-[2,3,4-tris-O-(3-carboxy-1-oxopropyl)-6-deoxy-α-L-mannopyranosyl]-β-D-glucopyranosyl}oxy}-4H-1-benzopyran-4-one

Conditions
ConditionsYield
With pyridine; dmap at 70℃; for 24h; Esterification;95%
540-51-2

2-bromoethanol

7085-55-4

troxerutin

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80 - 85℃;94.9%
100-39-0

benzyl bromide

183067-65-4

2-(3,4-bis(benzyloxy)phenyl)-7-(benzyloxy)-3,5-dihydroxy-4H-chromen-4-one

Conditions
ConditionsYield
Stage #1: benzyl bromide; rutin With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 3h; Inert atmosphere;
Stage #2: With hydrogenchloride In ethanol; water at 70℃; for 2h; regioselective reaction;
92%
Stage #1: rutin With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 16h; Cooling with ice;
81.2%
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 60h; Inert atmosphere;80%
Stage #1: benzyl bromide; rutin With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; for 0.25h;
Stage #2: With hydrogenchloride In ethanol; water; N,N-dimethyl-formamide at 78℃; for 2h;
43%
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 20 °C
2: hydrogenchloride / ethanol; water / 2 h / Reflux
View Scheme
74-88-4

methyl iodide

6068-80-0

2-(3,4-dimethoxyphenyl)-3,5-dihydroxy-7-methoxy-4H-chromen-4-one

Conditions
ConditionsYield
Stage #1: rutin; methyl iodide With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 3h; Inert atmosphere;
Stage #2: With hydrogenchloride In ethanol; water at 70℃; for 2h;
91%
75-21-8

oxirane

23869-24-1

7-mono-O-(β-hydroxyetyl)rutoside

Conditions
ConditionsYield
Stage #1: rutin With sodium tetraborate decahydrate In water at 40 - 45℃;
Stage #2: oxirane In water at 40 - 45℃; for 6h; Reagent/catalyst;
90.1%
Stage #1: rutin With sodium tetraborate decahydrate In water at 40 - 45℃;
Stage #2: oxirane In water at 40 - 45℃; for 6h; Reagent/catalyst;
84.8%
108-24-7

acetic anhydride

2328-13-4

2'',2''',3',3'',3''',4',4'',4''',5,7-deca-O-acetylrutin

Conditions
ConditionsYield
With pyridine; dmap at 20℃; for 12h; Inert atmosphere;90%
With pyridine; dmap at 20℃; for 12h; Inert atmosphere;90%
With dmap In pyridine at 20℃; for 18h;84%
107-07-3

2-chloro-ethanol

7085-55-4

troxerutin

Conditions
ConditionsYield
With potassium hydroxide at 68℃; for 24h; Temperature; Inert atmosphere;90%
With potassium carbonate In N,N-dimethyl-formamide for 0.133333h; Heating;

1333241-01-2

C22H11F3N2O11

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; for 15h;90%
79-03-8

propionyl chloride

C57H70O26

Conditions
ConditionsYield
With dmap In dichloromethane at 0 - 20℃; for 14h;73%
4407-36-7

(2E)-3-phenyl-2-propen-1-ol

85026-55-7

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol

Conditions
ConditionsYield
With α-L-rhamnosyl-β-D-glucosidase from Aspergillus niger In aq. phosphate buffer; dimethyl sulfoxide at 35℃; for 8h; pH=5; Enzymatic reaction;70%

C22H32O12

Conditions
ConditionsYield
With α-L-rhamnosyl-β-D-glucosidase from Aspergillus niger In aq. phosphate buffer; dimethyl sulfoxide at 35℃; for 8h; pH=5; Enzymatic reaction; regioselective reaction;70%
933-88-0

ortho-toluoyl chloride

C55H40O12

Conditions
ConditionsYield
With piperidine In N,N-dimethyl-formamide at 55℃; for 5h;68.1%
20649-40-5

(E)-4-(3-hydroxyprop-1-enyl)phenol

132294-76-9

4-hydroxycinnamyl alcohol 9-O-β-D-glucopyranoside

Conditions
ConditionsYield
With α-L-rhamnosyl-β-D-glucosidase from Aspergillus niger In aq. phosphate buffer; dimethyl sulfoxide at 35℃; for 8h; pH=5; Enzymatic reaction; regioselective reaction;68%
16331-45-6

p-ethylbenzoyl chloride

C60H50O12

Conditions
ConditionsYield
With piperidine In N,N-dimethyl-formamide at 62℃; for 4h;63.4%
Conditions
ConditionsYield
With α-L-rhamnosyl-β-D-glucosidase from Aspergillus niger K2 in Pichia pastoris In aq. phosphate buffer; dimethyl sulfoxide at 35 - 100℃; for 24h; pH=5; Enzymatic reaction;A 63%
B n/a
With rhamnodiastase Reactivity; Enzymatic reaction;
With rutinosidase In water Enzymatic reaction;
10025-69-1

tin(II) chloride dihdyrate

C54H56O32Sn

Conditions
ConditionsYield
Stage #1: tin(II) chloride dihdyrate; rutin In methanol at 20℃; for 0.5h;
Stage #2: With sodium methylate In methanol for 6h; pH=9; Reflux;
62%
122-01-0

4-chloro-benzoyl chloride

C50H25Cl5O12

Conditions
ConditionsYield
With piperidine In N,N-dimethyl-formamide at 74℃; for 4h;61.3%
6613-44-1

3,5-dimethylbenzoyl chloride

C60H50O12

Conditions
ConditionsYield
With piperidine In N,N-dimethyl-formamide at 58℃; for 4h;61.1%
100-39-0

benzyl bromide

C48H48O16

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 4h;61%
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 4h;61%
Stage #1: rutin With potassium carbonate In N,N-dimethyl-formamide for 0.5h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 60℃; for 3h;
103-80-0

phenylacetyl chloride

C55H40O12

Conditions
ConditionsYield
With piperidine In N,N-dimethyl-formamide at 57℃; for 4h;60.5%
Conditions
ConditionsYield
With hydrogenchloride; amalgamated zinc In methanol for 0.166667h;60%

A

B

117-39-5

quercetol

Conditions
ConditionsYield
With α-L-rhamnosyl-β-D-glucosidase from Aspergillus niger In dimethyl sulfoxide at 35℃; for 8h; pH=5; Enzymatic reaction;A 60%
B n/a
o-chlorobenzoyl chloride
609-65-4

o-chlorobenzoyl chloride

C50H25Cl5O12

Conditions
ConditionsYield
With piperidine In N,N-dimethyl-formamide at 75℃; for 4h;58.8%
108-24-7

acetic anhydride

1064-06-8

3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one

Conditions
ConditionsYield
With sulfuric acid at 65℃; for 6h;58.2%
53484-50-7

(E)-p-methoxy-cinnamyl alcohol

143729-77-5

4-methoxy-cinnamyl O-β-D-glucopyranoside

Conditions
ConditionsYield
With α-L-rhamnosyl-β-D-glucosidase from Aspergillus niger In aq. phosphate buffer; dimethyl sulfoxide at 35℃; for 8h; pH=5; Enzymatic reaction;58%
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  • Rutin     CAS: 153-18-4

  • Casno:

    153-18-4

    Rutin CAS: 153-18-4

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    Rutin Basic information Product Name: Rutin Synonyms: 3,3’,4’,5,7-pentahydroxy-flavon3-(o-rhamnosylglucos

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    Sophora Japonica Flower Extract Rutin English Name: Sophora Japonica Extract, Rutin Lating Name: Sophora Japonica L. Active Ingredients: Rutin Specification: Rutin 98% Test Method: UV Part of Plant Used: Flower Appearance: Yellow green fine

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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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