479-20-9

Basic information

• Product Name: ATRANORIN
• Synonyms: PARMELIN;USNARIN;ATRANORIN;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;ATRANORIN(P);Atrarin
• CAS NO: 479-20-9
• Molecular Formula: C₁₉H₁₈O₈
• Molecular Weight: 374.34
• EINECS: 207-527-7
• Mol File: 479-20-9.mol
• Article Data: 0

Chemical Properties

• Melting Point: 156-158°C
• Boiling Point: 535.7°C at 760 mmHg
• Flash Point: 189.3°C
• Appearance: /
• Density: 1.404g/cm³
• Vapor Pressure: 4.34E-12mmHg at 25°C
• Refractive Index: 1.644
• CAS DataBase Reference: ATRANORIN(CAS DataBase Reference)
• NIST Chemistry Reference: ATRANORIN(479-20-9)
• EPA Substance Registry System: ATRANORIN(479-20-9)

Safety Data

• Hazardous Substances Data: 479-20-9(Hazardous Substances Data)

Usage

Description

Atranorin is a depside lichen metabolite that has been found in S. alpinum and exhibits diverse biological activities. It possesses potent antimicrobial, anti-inflammatory, and antinociceptive properties, along with potential anticancer capabilities. Atranorin is a derivative compound of Chloratranorin (C364120), which are metabolites of Evernia prunastri, and it also functions as an antioxidant.
Used in Pharmaceutical Applications:
Atranorin is used as an antimicrobial agent for its activity against various bacteria, including B. cereus, B. subtilis, S. aureus, S. faecalis, P. vulgaris, L. monocytogenes, and A. hydrophila. It also shows effectiveness against fungi such as C. albicans and C. glabrata, as well as the mycobacterium M. aurum.
Atranorin is used as an antinociceptive agent for its ability to inhibit acetic acid-induced writhing in mice when administered orally at doses of 200 and 400 mg/kg.
Atranorin is used as an anti-inflammatory agent for its effectiveness in reducing paw licking and biting in the second phase of the formalin test when administered 30 minutes prior to formalin in mice.
Used in Cosmetic Applications:
Atranorin is used as a component in extracts of oak moss, which are utilized as a fragrance in the cosmetic industry.
Used in Anticancer Applications:
Although not explicitly mentioned in the provided materials, Atranorin's cytotoxicity to certain cancer cells (A270, HL-60, and Jurkat) suggests potential use as an anticancer agent. Further research would be required to explore this application fully.
Used in Antioxidant Applications:
Atranorin functions as an antioxidant, which could have various applications in different industries, such as pharmaceuticals, cosmetics, and the food industry, to protect against oxidative stress and maintain product stability.

Hazard

A poison by skin contact. A skin irritant.

Safety Profile

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

InChI:InChI=1/C19H18O8/c1-8-5-12(21)11(7-20)17(23)15(8)19(25)27-13-6-9(2)14(18(24)26-4)16(22)10(13)3/h5-7,21-23H,1-4H3

Synthetic route

atranorin (479-20-9) → methyl 3-α-hydroxy-4-O-demethylbarbatate

Conditions	Yield
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) + physodalic acid (90689-60-4) → 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	Yield
With toluene-4-sulfonic acid In 1,4-dioxane for 4h; Heating;	91%

atranorin (479-20-9) + 4-methylphenoxyacetyl hydrazide (36304-39-9) → C28H28N2O9

Conditions	Yield
With acetic acid In ethanol at 50℃; for 2h;	89%

m-tolyloxy-acetic acid hydrazide (36304-38-8) + atranorin (479-20-9) → C28H28N2O9

Conditions	Yield
With acetic acid In ethanol at 50℃; for 2h;	86.6%

atranorin (479-20-9) + o-tolyloxyacetic acid hydrazide (36304-37-7) → C28H28N2O9

Conditions	Yield
With acetic acid In ethanol at 50℃; for 2h;	86%

atranorin (479-20-9) + 2-[(4-methylphenyl)amino]acetohydrazide (2350-99-4) → C28H29N3O8

Conditions	Yield
With acetic acid In ethanol at 50℃; for 2h;	83%

atranorin (479-20-9) + 5-chlorosalicylhydrazide (5022-48-0) → C26H23ClN2O9

Conditions	Yield
With acetic acid In ethanol at 50℃; for 2h;	83%

atranorin (479-20-9) + 1-(2-naphthyloxyacetyl)hydrazine (36304-47-9) → C31H28N2O9

Conditions	Yield
With acetic acid In ethanol at 50℃; for 2h;	82.6%

atranorin (479-20-9) + 2-phenylacetylhydrazine (937-39-3) → C27H26N2O8

Conditions	Yield
With acetic acid In ethanol at 50℃; for 2h;	82%

atranorin (479-20-9) + [(1,3-benzothiazol-2-ylthio)acetyl]hydrazine (24044-91-5) → C28H25N3O8S2

Conditions	Yield
With acetic acid In ethanol at 50℃; for 2h;	81.2%

atranorin (479-20-9) + 2-(4-bromophenoxy)acetic acid hydrazide (16738-00-4) → C27H25BrN2O9

Conditions	Yield
With acetic acid In ethanol at 50℃; for 2h;	73.3%

atranorin (479-20-9) + 2-hydroxy-5-iodobenzohydrazide (31822-04-5) → C26H23IN2O9

Conditions	Yield
With acetic acid In ethanol at 50℃; for 2h;	73.3%

atranorin (479-20-9) + 2-isopropyl-5-methylphenoxyacetylhydrazide (75843-51-5) → C31H34N2O9

Conditions	Yield
With acetic acid In ethanol at 50℃; for 2h;	52.7%

benzo[b]furan-2-carbohydrazide (42974-19-6) + atranorin (479-20-9) → C28H24N2O9

Conditions	Yield
With acetic acid In ethanol at 50℃; for 2h;	50.7%

propan-1-ol (71-23-8) + atranorin (479-20-9) → 3-formyl-2,4-dihydroxy-6-methyl-benzoic acid propyl ester

Conditions	Yield
With alkali at 150℃; im Rohr;

ethanol (64-17-5) + atranorin (479-20-9) → 2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester (4707-47-5) + ethyl hematommate (39503-14-5)

Conditions	Yield
With alkali at 150℃; im Rohr;

i-Amyl alcohol (123-51-3) + atranorin (479-20-9) → 2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester (4707-47-5) + 3-formyl-2,4-dihydroxy-6-methyl-benzoic acid isopentyl ester

Conditions	Yield
With alkali at 150℃; im Rohr;

atranorin (479-20-9) → atranol (526-37-4)

Conditions	Yield
With formic acid
With water at 150℃;
With sodium carbonate

atranorin (479-20-9) → 2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester (4707-47-5)

Conditions	Yield
With acetic acid
With water
With ethanol

atranorin (479-20-9) → 2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester (4707-47-5) + methyl haematommate (34874-90-3)

Conditions	Yield
With methanol at 150℃; im Rohr;

atranorin (479-20-9) → 2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester (4707-47-5) + 2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid ethyl ester (62392-82-9)

Conditions	Yield
With ethanol; aniline

atranorin (479-20-9) → acide formyl-3-dihydroxy-2,4-methyl-6-benzoique (479-25-4)

Conditions	Yield
With potassium hydroxide

atranorin (479-20-9) → methyl 4-(2,4-dihydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate (5038-46-0)

Conditions	Yield
With palladium on activated charcoal; acetic acid Hydrogenation;

atranorin (479-20-9) → 4-(3-formyl-2,4-dihydroxy-6-methyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoic acid

Conditions	Yield
With acetic acid at 80℃;

atranorin (479-20-9) + acetic anhydride (108-24-7) → 2-acetoxy-4-(2,4-diacetoxy-3-diacetoxymethyl-6-methyl-benzoyloxy)-3,6-dimethyl-benzoic acid methyl ester (15257-10-0)

Conditions	Yield
With perchloric acid

atranorin (479-20-9) + acetic anhydride (108-24-7) → 2-acetoxy-4-(2,4-diacetoxy-3-formyl-6-methyl-benzoyloxy)-3,6-dimethyl-benzoic acid methyl ester (15222-51-2)

Conditions	Yield
With pyridine

atranorin (479-20-9) + acetic acid (64-19-7) → 4-(3-formyl-2,4-dihydroxy-6-methyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoic acid

Conditions	Yield
at 80℃; beim Eindunsten;

methanol (67-56-1) + atranorin (479-20-9) + aniline (62-53-3) → 2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid methyl ester

ethanol (64-17-5) + atranorin (479-20-9) + aniline (62-53-3) → 2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester (4707-47-5) + 2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid ethyl ester (62392-82-9)

atranorin (479-20-9) + aniline (62-53-3) → 2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester (4707-47-5) + 2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid methyl ester

Conditions	Yield
With methanol

Downstream Products

• 4707-47-5 2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester 
• 504-15-4 orcinol 
• 526-37-4 atranol 
• 488-87-9 2,5-dimethyl-1,3-benzenediol 
• 34874-90-3 methyl haematommate 
• 125304-80-5 methyl baeomycesate 
• 479-16-3 chloroatranorin