Product Name

  • Name

    ATRANORIN

  • EINECS
  • CAS No. 479-20-9
  • Density 1.404g/cm3
  • Solubility
  • Melting Point 156-158°C
  • Formula C19H18 O8
  • Boiling Point 535.7°C at 760 mmHg
  • Molecular Weight 374.347
  • Flash Point 189.3°C
  • Transport Information
  • Appearance
  • Safety A poison by skin contact. A skin irritant. When heated to decomposition it emits acrid smoke and irritating vapors.
  • Risk Codes
  • Molecular Structure Molecular Structure of 479-20-9 (ATRANORIN)
  • Hazard Symbols A poison by skin contact. A skin irritant.
  • Synonyms Atranoricacid (6CI); Isophthalaldehydic acid, 2,4-dihydroxy-6-methyl-, 4-ester withmethyl 3,6-dimethyl-b-resorcylate (8CI); Antranorin; Atranorin; Atranorine; NSC 249980; NSC685591; NSC 87512; Parmelin; Parmelin acid; Usnarin; Usnarin acid
  • PSA 130.36000
  • LogP 2.54690

Synthetic route

atranorin
479-20-9

atranorin

methyl 3-α-hydroxy-4-O-demethylbarbatate

methyl 3-α-hydroxy-4-O-demethylbarbatate

Conditions
ConditionsYield
With sodium tetrahydroborate; ethanol In 1,2-dimethoxyethane for 16h;99%
With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h;84%
atranorin
479-20-9

atranorin

physodalic acid
90689-60-4

physodalic acid

4-formyl-3,8-dihydroxy-9-(2,4-dihydroxy-5-methoxycarbonyl-3,6-dimethylbenzyl)-1,6-dimethyl-11-oxo-11H-dibenzo<1,4>dioxepin-7-carboxylic acid

4-formyl-3,8-dihydroxy-9-(2,4-dihydroxy-5-methoxycarbonyl-3,6-dimethylbenzyl)-1,6-dimethyl-11-oxo-11H-dibenzo<1,4>dioxepin-7-carboxylic acid

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 1,4-dioxane for 4h; Heating;91%
atranorin
479-20-9

atranorin

4-methylphenoxyacetyl hydrazide
36304-39-9

4-methylphenoxyacetyl hydrazide

C28H28N2O9

C28H28N2O9

Conditions
ConditionsYield
With acetic acid In ethanol at 50℃; for 2h;89%
m-tolyloxy-acetic acid hydrazide
36304-38-8

m-tolyloxy-acetic acid hydrazide

atranorin
479-20-9

atranorin

C28H28N2O9

C28H28N2O9

Conditions
ConditionsYield
With acetic acid In ethanol at 50℃; for 2h;86.6%
atranorin
479-20-9

atranorin

o-tolyloxyacetic acid hydrazide
36304-37-7

o-tolyloxyacetic acid hydrazide

C28H28N2O9

C28H28N2O9

Conditions
ConditionsYield
With acetic acid In ethanol at 50℃; for 2h;86%
atranorin
479-20-9

atranorin

2-[(4-methylphenyl)amino]acetohydrazide
2350-99-4

2-[(4-methylphenyl)amino]acetohydrazide

C28H29N3O8

C28H29N3O8

Conditions
ConditionsYield
With acetic acid In ethanol at 50℃; for 2h;83%
atranorin
479-20-9

atranorin

5-chlorosalicylhydrazide
5022-48-0

5-chlorosalicylhydrazide

C26H23ClN2O9

C26H23ClN2O9

Conditions
ConditionsYield
With acetic acid In ethanol at 50℃; for 2h;83%
atranorin
479-20-9

atranorin

1-(2-naphthyloxyacetyl)hydrazine
36304-47-9

1-(2-naphthyloxyacetyl)hydrazine

C31H28N2O9

C31H28N2O9

Conditions
ConditionsYield
With acetic acid In ethanol at 50℃; for 2h;82.6%
atranorin
479-20-9

atranorin

2-phenylacetylhydrazine
937-39-3

2-phenylacetylhydrazine

C27H26N2O8

C27H26N2O8

Conditions
ConditionsYield
With acetic acid In ethanol at 50℃; for 2h;82%
atranorin
479-20-9

atranorin

[(1,3-benzothiazol-2-ylthio)acetyl]hydrazine
24044-91-5

[(1,3-benzothiazol-2-ylthio)acetyl]hydrazine

C28H25N3O8S2

C28H25N3O8S2

Conditions
ConditionsYield
With acetic acid In ethanol at 50℃; for 2h;81.2%
atranorin
479-20-9

atranorin

2-(4-bromophenoxy)acetic acid hydrazide
16738-00-4

2-(4-bromophenoxy)acetic acid hydrazide

C27H25BrN2O9

C27H25BrN2O9

Conditions
ConditionsYield
With acetic acid In ethanol at 50℃; for 2h;73.3%
atranorin
479-20-9

atranorin

2-hydroxy-5-iodobenzohydrazide
31822-04-5

2-hydroxy-5-iodobenzohydrazide

C26H23IN2O9

C26H23IN2O9

Conditions
ConditionsYield
With acetic acid In ethanol at 50℃; for 2h;73.3%
atranorin
479-20-9

atranorin

2-isopropyl-5-methylphenoxyacetylhydrazide
75843-51-5

2-isopropyl-5-methylphenoxyacetylhydrazide

C31H34N2O9

C31H34N2O9

Conditions
ConditionsYield
With acetic acid In ethanol at 50℃; for 2h;52.7%
benzo[b]furan-2-carbohydrazide
42974-19-6

benzo[b]furan-2-carbohydrazide

atranorin
479-20-9

atranorin

C28H24N2O9

C28H24N2O9

Conditions
ConditionsYield
With acetic acid In ethanol at 50℃; for 2h;50.7%
propan-1-ol
71-23-8

propan-1-ol

atranorin
479-20-9

atranorin

3-formyl-2,4-dihydroxy-6-methyl-benzoic acid propyl ester

3-formyl-2,4-dihydroxy-6-methyl-benzoic acid propyl ester

Conditions
ConditionsYield
With alkali at 150℃; im Rohr;
ethanol
64-17-5

ethanol

atranorin
479-20-9

atranorin

A

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

B

ethyl hematommate
39503-14-5

ethyl hematommate

Conditions
ConditionsYield
With alkali at 150℃; im Rohr;
...Expand
i-Amyl alcohol
123-51-3

i-Amyl alcohol

atranorin
479-20-9

atranorin

A

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

B

3-formyl-2,4-dihydroxy-6-methyl-benzoic acid isopentyl ester

3-formyl-2,4-dihydroxy-6-methyl-benzoic acid isopentyl ester

Conditions
ConditionsYield
With alkali at 150℃; im Rohr;
...Expand
atranorin
479-20-9

atranorin

atranol
526-37-4

atranol

Conditions
ConditionsYield
With formic acid
With water at 150℃;
With sodium carbonate
atranorin
479-20-9

atranorin

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
With acetic acid
With water
With ethanol
atranorin
479-20-9

atranorin

A

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

B

methyl haematommate
34874-90-3

methyl haematommate

Conditions
ConditionsYield
With methanol at 150℃; im Rohr;
atranorin
479-20-9

atranorin

A

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

B

2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid ethyl ester
62392-82-9

2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid ethyl ester

Conditions
ConditionsYield
With ethanol; aniline
atranorin
479-20-9

atranorin

acide formyl-3-dihydroxy-2,4-methyl-6-benzoique
479-25-4

acide formyl-3-dihydroxy-2,4-methyl-6-benzoique

Conditions
ConditionsYield
With potassium hydroxide
atranorin
479-20-9

atranorin

methyl 4-(2,4-dihydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate
5038-46-0

methyl 4-(2,4-dihydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate

Conditions
ConditionsYield
With palladium on activated charcoal; acetic acid Hydrogenation;
atranorin
479-20-9

atranorin

4-(3-formyl-2,4-dihydroxy-6-methyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoic acid

4-(3-formyl-2,4-dihydroxy-6-methyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoic acid

Conditions
ConditionsYield
With acetic acid at 80℃;
atranorin
479-20-9

atranorin

acetic anhydride
108-24-7

acetic anhydride

2-acetoxy-4-(2,4-diacetoxy-3-diacetoxymethyl-6-methyl-benzoyloxy)-3,6-dimethyl-benzoic acid methyl ester
15257-10-0

2-acetoxy-4-(2,4-diacetoxy-3-diacetoxymethyl-6-methyl-benzoyloxy)-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
With perchloric acid
atranorin
479-20-9

atranorin

acetic anhydride
108-24-7

acetic anhydride

2-acetoxy-4-(2,4-diacetoxy-3-formyl-6-methyl-benzoyloxy)-3,6-dimethyl-benzoic acid methyl ester
15222-51-2

2-acetoxy-4-(2,4-diacetoxy-3-formyl-6-methyl-benzoyloxy)-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
With pyridine
atranorin
479-20-9

atranorin

acetic acid
64-19-7

acetic acid

4-(3-formyl-2,4-dihydroxy-6-methyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoic acid

4-(3-formyl-2,4-dihydroxy-6-methyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoic acid

Conditions
ConditionsYield
at 80℃; beim Eindunsten;
methanol
67-56-1

methanol

atranorin
479-20-9

atranorin

aniline
62-53-3

aniline

2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid methyl ester

2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid methyl ester

...Expand
ethanol
64-17-5

ethanol

atranorin
479-20-9

atranorin

aniline
62-53-3

aniline

A

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

B

2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid ethyl ester
62392-82-9

2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid ethyl ester

...Expand
atranorin
479-20-9

atranorin

aniline
62-53-3

aniline

A

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

B

2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid methyl ester

2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid methyl ester

Conditions
ConditionsYield
With methanol
...Expand

ATRANORIN Chemical Properties

Atranorin is also named as Parmelin;Usnarin;3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 3-formyl-2,4-dihydroxy-6-methylbenzoate;3-Formyl-2,4-dihydroxy-6-methylbenzoic acid 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester;NSC-685591,and so on. Atranorin is usually colorless crystal or crystalline powder.

CAS: 479-20-9
Molecular Formula: C19H18O8
Molecular Weight: 374.34
EINECS: 207-527-7
Molecular structure:
Melting point:  156-158°C

ATRANORIN Uses

Atranorin is commonly used as anti-microbial drugs and anti-bacteria drugs.

ATRANORIN Toxicity Data With Reference

1.   

skn-gpg 5%

   CODEDG    Contact Dermatitis. Environmental and Occupational Dermatitis. 11 (1984),168.
2.   

skn-gpg TDLo:1 pph

   CODEDG    Contact Dermatitis. Environmental and Occupational Dermatitis. 11 (1984),168.

ATRANORIN Safety Profile

A poison by skin contact. A skin irritant. When heated to decomposition it emits acrid smoke and irritating vapors.

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