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117-02-2

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117-02-2 Usage

Description

Rubiadin is an anthraquinone that is a minor component of certain Rubia species, as well as other plants. It demonstrates antioxidant activity.

Uses

Rubiadin is a dihydroxy anthraquinone isolated from Rubia cordifolia. Rubiadin exhibits anti-epileptic activity in mice.

Definition

ChEBI: A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 3 and a methyl group at position 2. It has been isolated from Rubia yunnanensis.

Check Digit Verification of cas no

The CAS Registry Mumber 117-02-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 7 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 117-02:
(5*1)+(4*1)+(3*7)+(2*0)+(1*2)=32
32 % 10 = 2
So 117-02-2 is a valid CAS Registry Number.
InChI:InChI=1/C15H10O4/c1-7-11(16)6-10-12(13(7)17)15(19)9-5-3-2-4-8(9)14(10)18/h2-6,16-17H,1H3

117-02-2 Well-known Company Product Price

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  • Sigma-Aldrich

  • (74553)  Rubiadin  analytical standard

  • 117-02-2

  • 74553-10MG

  • 7,236.45CNY

  • Detail

117-02-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name rubiadin

1.2 Other means of identification

Product number -
Other names Rubiadine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:117-02-2 SDS

117-02-2Synthetic route

phthalic anhydride
85-44-9

phthalic anhydride

2-methylbenzene-1,3-diol
608-25-3

2-methylbenzene-1,3-diol

rubiadin
117-02-2

rubiadin

Conditions
ConditionsYield
With aluminum (III) chloride; sodium chloride at 165 - 175℃; for 1h; Friedel-Crafts Acylation;65%
With aluminum (III) chloride; sodium chloride at 130 - 170℃; for 0.75h;64%
With aluminum (III) chloride; sodium chloride at 165 - 170℃; for 0.75h; Friedel-Crafts Acylation;40%
With aluminum (III) chloride; sodium chloride
With aluminum (III) chloride Microwave irradiation;
1,3-dimethoxy-2-methylanthraquinone
22170-88-3

1,3-dimethoxy-2-methylanthraquinone

rubiadin
117-02-2

rubiadin

Conditions
ConditionsYield
With hydrogen bromide; acetic acid
1-hydroxy-3-methoxy-2-methyl-9,10-anthraquinone
22170-89-4

1-hydroxy-3-methoxy-2-methyl-9,10-anthraquinone

rubiadin
117-02-2

rubiadin

Conditions
ConditionsYield
With aluminium trichloride at 200℃; durch langsames Erhitzen;
With hydrogen bromide; acetic acid
rubiadin-1-methyl ether
7460-43-7

rubiadin-1-methyl ether

rubiadin
117-02-2

rubiadin

Conditions
ConditionsYield
With sulfuric acid at 150℃; durch kurzes Erhitzen (10 min);
3,5-dihydroxy-4-methylbenzoic acid
28026-96-2

3,5-dihydroxy-4-methylbenzoic acid

benzoic acid
65-85-0

benzoic acid

rubiadin
117-02-2

rubiadin

Conditions
ConditionsYield
With sulfuric acid at 120℃;
With sulfuric acid at 110 - 120℃;
2-chloro-1,4-naphthoquinone
1010-60-2

2-chloro-1,4-naphthoquinone

(Z)-1-Ethoxy-2-methyl-1,3-bis-trimethylsilanyloxy-buta-1,3-diene
122305-38-8

(Z)-1-Ethoxy-2-methyl-1,3-bis-trimethylsilanyloxy-buta-1,3-diene

rubiadin
117-02-2

rubiadin

Conditions
ConditionsYield
With hydrogenchloride 1.) benzene, r.t., 20-72 h; 2.) THF, r.t., 1-3 h; 3.) reflux, 1-5 h; Multistep reaction;
rubiadin-1-methyl ether

rubiadin-1-methyl ether

rubiadin
117-02-2

rubiadin

Conditions
ConditionsYield
With hydrogenchloride at 140 - 150℃;
1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

1,2,4-trihydroxy-3-methyl-anthraquinone
7485-42-9

1,2,4-trihydroxy-3-methyl-anthraquinone

SnCl2

SnCl2

rubiadin
117-02-2

rubiadin

3-methoxy-2-methylphenol
6971-52-4

3-methoxy-2-methylphenol

rubiadin
117-02-2

rubiadin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
2: aluminium chloride; carbon disulfide
3: fuming sulfuric acid
4: AlCl3 / 200 °C / durch langsames Erhitzen
View Scheme
2,6-dimethoxytoluene
5673-07-4

2,6-dimethoxytoluene

rubiadin
117-02-2

rubiadin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aluminium chloride; carbon disulfide
2: fuming sulfuric acid
3: AlCl3 / 200 °C / durch langsames Erhitzen
View Scheme
6-methoxy-2-nitrotoluene
4837-88-1

6-methoxy-2-nitrotoluene

rubiadin
117-02-2

rubiadin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: tin; aqueous hydrochloric acid
2: aqueous H2SO4 / Diazotization
4: aluminium chloride; carbon disulfide
5: fuming sulfuric acid
6: AlCl3 / 200 °C / durch langsames Erhitzen
View Scheme
2-(2,4-dimethoxy-3-methyl-benzoyl)-benzoic acid

2-(2,4-dimethoxy-3-methyl-benzoyl)-benzoic acid

rubiadin
117-02-2

rubiadin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: fuming sulfuric acid
2: AlCl3 / 200 °C / durch langsames Erhitzen
View Scheme
2-methyl-3-methoxyaniline
19500-02-8

2-methyl-3-methoxyaniline

rubiadin
117-02-2

rubiadin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: aqueous H2SO4 / Diazotization
3: aluminium chloride; carbon disulfide
4: fuming sulfuric acid
5: AlCl3 / 200 °C / durch langsames Erhitzen
View Scheme
1,3-dichloro-2-methyl-anthraquinone
18018-09-2

1,3-dichloro-2-methyl-anthraquinone

rubiadin
117-02-2

rubiadin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: aqueous HBr; acetic acid
View Scheme
rubiadin
117-02-2

rubiadin

dimethyl sulfate
77-78-1

dimethyl sulfate

1,3-dimethoxy-2-methylanthraquinone
22170-88-3

1,3-dimethoxy-2-methylanthraquinone

Conditions
ConditionsYield
With potassium carbonate In acetone for 22h; Reflux;100%
With potassium carbonate; acetone
rubiadin
117-02-2

rubiadin

acetic anhydride
108-24-7

acetic anhydride

3-acetoxy-1-hydroxy-2-methylanthraquinone
10383-64-9

3-acetoxy-1-hydroxy-2-methylanthraquinone

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 20h;100%
With potassium carbonate In acetone
2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride
52162-55-7, 69256-45-7, 61826-14-0

2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride

rubiadin
117-02-2

rubiadin

C34H30O7

C34H30O7

Conditions
ConditionsYield
Stage #1: rubiadin With sodium hydride In acetonitrile; mineral oil at 0℃; for 0.166667h;
Stage #2: 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride at 20℃; for 0.333333h;
93%
rubiadin
117-02-2

rubiadin

4-bromo-1,3-dihydroxy-2-methylanthraquinone
100914-52-1

4-bromo-1,3-dihydroxy-2-methylanthraquinone

Conditions
ConditionsYield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 24h; Reflux;60%
With bromine; sodium acetate; acetic acid
triacetoxyborane
4887-24-5

triacetoxyborane

rubiadin
117-02-2

rubiadin

3-acetoxy-1-diacetoxyboranyloxy-2-methyl-anthraquinone

3-acetoxy-1-diacetoxyboranyloxy-2-methyl-anthraquinone

Conditions
ConditionsYield
With acetic anhydride
rubiadin
117-02-2

rubiadin

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

1-hydroxy-2-methyl-3-(tetra-O-acetyl-β-D-glucopyranosyloxy)-anthraquinone
904795-74-0

1-hydroxy-2-methyl-3-(tetra-O-acetyl-β-D-glucopyranosyloxy)-anthraquinone

Conditions
ConditionsYield
With sodium hydroxide; acetone
rubiadin
117-02-2

rubiadin

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

2-methyl-1,3-bis-(tetra-O-acetyl-β-D-glucopyranosyloxy)-anthraquinone

2-methyl-1,3-bis-(tetra-O-acetyl-β-D-glucopyranosyloxy)-anthraquinone

Conditions
ConditionsYield
With quinoline; silver(l) oxide
rubiadin
117-02-2

rubiadin

rubiadin-1-methyl ether
7460-43-7

rubiadin-1-methyl ether

Conditions
ConditionsYield
(methylation);
rubiadin
117-02-2

rubiadin

acetic anhydride
108-24-7

acetic anhydride

rubiadin diacetate
7416-31-1

rubiadin diacetate

Conditions
ConditionsYield
With pyridine
With potassium carbonate
rubiadin
117-02-2

rubiadin

3-β-D-glucopyranosyloxy-1-hydroxy-2-methyl-anthraquinone
57186-30-8

3-β-D-glucopyranosyloxy-1-hydroxy-2-methyl-anthraquinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetone; aq. NaOH solution
2: methanol; aq. NaOH solution
View Scheme
rubiadin
117-02-2

rubiadin

1-methoxy-2-methyl-3-(tetra-O-acetyl-β-D-glucopyranosyloxy)-anthraquinone

1-methoxy-2-methyl-3-(tetra-O-acetyl-β-D-glucopyranosyloxy)-anthraquinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetone; aq. NaOH solution
2: acetone; silver oxide
View Scheme
rubiadin
117-02-2

rubiadin

1-acetoxy-2-methyl-3-(tetra-O-acetyl-β-D-glucopyranosyloxy)-anthraquinone

1-acetoxy-2-methyl-3-(tetra-O-acetyl-β-D-glucopyranosyloxy)-anthraquinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetone; aq. NaOH solution
2: pyridine
View Scheme
rubiadin
117-02-2

rubiadin

3-acetoxy-1-methoxy-2-methylanthraquinone
2324-25-6

3-acetoxy-1-methoxy-2-methylanthraquinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / acetone / 20 h / 20 °C
2: potassium carbonate / acetone / 22 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / acetone
2: potassium carbonate; dimethyl sulfate / acetone / 22 h / Reflux
View Scheme
rubiadin
117-02-2

rubiadin

1-methoxy-3-acetoxy-2-bromomethyl-1-methoxyathraquinone
63965-55-9

1-methoxy-3-acetoxy-2-bromomethyl-1-methoxyathraquinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / acetone / 20 h / 20 °C
2: potassium carbonate / acetone / 22 h / Reflux
3: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 24 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / acetone
2: potassium carbonate; dimethyl sulfate / acetone / 22 h / Reflux
3: N-Bromosuccinimide / tetrachloromethane / 30 h / Reflux
View Scheme
rubiadin
117-02-2

rubiadin

2-ethoxymethyl-3-hydroxy-1-methoxyanthracene-9,10-dione
63965-57-1

2-ethoxymethyl-3-hydroxy-1-methoxyanthracene-9,10-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate / acetone / 20 h / 20 °C
2: potassium carbonate / acetone / 22 h / Reflux
3: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 24 h / Reflux
4: sodium hydroxide / water / 24 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / acetone
2.1: potassium carbonate; dimethyl sulfate / acetone / 22 h / Reflux
3.1: N-Bromosuccinimide / tetrachloromethane / 30 h / Reflux
4.1: sodium hydroxide; water / ethanol
4.2: Reflux
View Scheme

117-02-2Relevant articles and documents

-

Mitter

, (1928)

-

Design, Synthesis, Molecular Docking, and Biological Evaluation of New Emodin Anthraquinone Derivatives as Potential Antitumor Substances

Li, Yuying,Guo, Fang,Chen, Tinggui,Zhang, Liwei,Wang, Zhuanhua,Su, Qiang,Feng, Liheng

, (2020)

The emodin anthraquinone derivatives are generally used in traditional Chinese medicine due to their various pharmacological activities. In the present study, a series of emodin anthraquinone derivatives have been designed and synthesized, among which 1,3-dihydroxy-6,8-dimethoxyanthracene-9,10-dione is a natural compound that has been synthesized for the very first time, and 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione is a compound that has never been reported earlier. Interestingly, while total seven of these compounds showed neuraminidase inhibitory activity in influenza virus with inhibition rate more than 50 %, specific four compounds exhibited significant inhibition of tumor cell proliferation. The further results demonstrate that 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione showed the best anticancer activity among all the synthesized compounds by inducing highest apoptosis rate to HCT116 cancer cells and arresting their G0/G1 cell cycle phase, through elevation of intracellular level of reactive oxygen species (ROS). Moreover, the binding of 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione with BSA protein has thoroughly been investigated. Altogether, this study suggests the neuraminidase inhibitory activity and antitumor potential of the new emodin anthraquinone derivatives.

Method for synthesizing 2,6-dihydroxytoluene by using waste acid

-

, (2021/08/07)

The invention discloses a method for synthesizing 2,6-dihydroxytoluene by using waste acid mechanically. According to the method, 3-chloro-2-methylaniline is taken as a raw material, an intermediate 3-chloro-2-methylphenol is synthesized through diazotization and hydrolysis, the reaction is optimized in the alkali fusion, acidification and refining processes, the mechanical application of waste acid and a solvent in the reaction and the optimization of a refining scheme are emphatically optimized, the yield is effectively improved, three wastes are reduced, and 2,6-dihydroxytoluene is synthesized. The method provided by the invention greatly reduces the generation of acidic wastewater, better meets the requirement of environmental protection, and effectively increases the yield of the product, and the quality of the product reaches 99.0-99.5%.

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