500-67-4

Basic information

• Product Name: 5-Heptylresorcinol
• Synonyms: SPHEROPHORAL;1,3-Benzenediol, 5-heptyl-;5-Heptyl-1,3-benzenediol;5-HEPTYLRESORCINOL;5-HEPTYLRESORCINOL 95%;5-Heptylbenzene-1,3-diol
• CAS NO: 500-67-4
• Molecular Formula: C₁₃H₂₀O₂
• Molecular Weight: 208.3
• EINECS: 207-909-3
• Mol File: 500-67-4.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 342.3 °C at 760 mmHg
• Flash Point: 159.5 °C
• Appearance: /
• Density: 1.033 g/cm³
• Vapor Pressure: 3.83E-05mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 5-Heptylresorcinol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Heptylresorcinol(500-67-4)
• EPA Substance Registry System: 5-Heptylresorcinol(500-67-4)

Safety Data

• Hazardous Substances Data: 500-67-4(Hazardous Substances Data)

Usage

Uses

5-Heptylresorcinol and other alkylhydroxybenzenes have been used to study the protective effect in Saccharomyces cerevisiae against oxidative and radiation-caused damage.

InChI:InChI=1/C13H20O2/c1-2-3-4-5-6-7-11-8-12(14)10-13(15)9-11/h8-10,14-15H,2-7H2,1H3

Synthetic route

5-n-heptyl resorcinol dimethyl ether (6121-64-8) → spherophorol (500-67-4)

Conditions	Yield
With boron tribromide In dichloromethane at 0 - 25℃; ether cleavage;	100%
With hydrogen bromide; acetic acid In water at 125℃; for 3h; Inert atmosphere;	96%
With boron tribromide In dichloromethane at -78 - 0℃;	91%

2,2-dimethyl-5-(1-heptyl)-7-hydroxy-4H-1,3-benzodioxin-4-one (137571-77-8) → spherophorol (500-67-4)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 115℃; for 4.5h;	99%
With aqueous KOH In dimethyl sulfoxide	270 mg (99%)

sphaerophorin (529-56-6) → spherophorol (500-67-4)

Conditions	Yield
With potassium hydroxide

2-Bromo-5-heptyl-3-hydroxy-cyclohex-2-enone (70336-35-5) → spherophorol (500-67-4)

Conditions	Yield
With acetic acid

ethyl 2-heptyl-4,6-dihydroxybenzoate (38862-66-7) → spherophorol (500-67-4)

Conditions	Yield
With sodium hydroxide In water Heating;

sphaerophorolcarboxylic acid (6121-76-2) → spherophorol (500-67-4)

Conditions	Yield
at 170℃;

methyl 2,4-dihydroxy-6-heptylbenzoate (6121-77-3) → spherophorol (500-67-4)

Conditions	Yield
With hydrogenchloride; potassium hydroxide 1.) DMSO, 115 deg C, 2.5 h, 2.) 0 deg C, 3 d; Yield given. Multistep reaction;

triethylammonium salt of sphaerophorin → spherophorol (500-67-4) + O-methylorcinol (3209-13-0) + 3-methoxy-5-methylphenyl 2-hydroxy-4-methoxy-6-methylbenzoate + decarboxysphaerophorin

Conditions	Yield
at 180℃; for 0.166667h; Product distribution; pyrolysis;

diethyl 1,3-acetonedicarboxylate (105-50-0) + 3-oxo-decanoic acid (1)-ethyl ester → spherophorol (500-67-4)

Conditions	Yield
With sodium at 150 - 180℃; Verschmelzen des Reaktionsprodukts mit KOH bei 250grad;

sphaerophorin (529-56-6) + ethanolic KOH-solution → spherophorol (500-67-4) + 2-hydroxy-4-methoxy-6-methylbenzoic acid (570-10-5)

Conditions	Yield

3,5-dimethoxy-1-(1-heptenyl)benzene (23815-39-6) → spherophorol (500-67-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / H2 / Pd/C / ethyl acetate / 20 °C 2: 91 percent / BBr3 / CH2Cl2 / -78 - 0 °C View Scheme
Multi-step reaction with 2 steps 1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 2 h 2: acetic acid; hydrogen bromide / water / 3 h / 125 °C / Inert atmosphere View Scheme

3,5-dimethoxybenzaldehdye (7311-34-4) → spherophorol (500-67-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / diethyl ether / 2 h / Heating 2: 73 percent / trifluoroacetic acid; hydrogen / Pd/C / ethanol / 168 h / 2585.74 Torr 3: 100 percent / BBr3 / CH2Cl2 / 0 - 25 °C View Scheme
Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 2 h 3.1: acetic acid; hydrogen bromide / water / 3 h / 125 °C / Inert atmosphere View Scheme

spherophorol (500-67-4) + (-)-trans-carveol (18383-51-2) → JWH 091

Conditions	Yield
With toluene-4-sulfonic acid In benzene at 80℃; for 3h; Cyclization;	57%

spherophorol (500-67-4) + (1S,4R)-p-mentha-2,8-dien-1-ol (22972-51-6) → 5-heptyl-2-((1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-enyl)benzene-1,3-diol (55824-13-0)

Conditions	Yield
With toluene-4-sulfonic acid In benzene at 10 - 20℃;	32%

spherophorol (500-67-4) + (-)-trans-Isopiperitenol (74410-00-7) → 5-heptyl-2-((1S,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-enyl)benzene-1,3-diol + C23H34O2 + C33H48O2

Conditions	Yield
With aluminum oxide; boron trifluoride diethyl etherate In dichloromethane for 0.00277778h; Inert atmosphere; Reflux;	A 22% B 6% C 11%

Upstream product

• 70336-35-5 2-Bromo-5-heptyl-3-hydroxy-cyclohex-2-enone 
• 6121-76-2 sphaerophorolcarboxylic acid 
• 137571-77-8 2,2-dimethyl-5-(1-heptyl)-7-hydroxy-4H-1,3-benzodioxin-4-one 
• 105-50-0 diethyl 1,3-acetonedicarboxylate 
• 17213-57-9 3,5-dimethoxybenzoyl chloride 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 17213-58-0 3,5-dimethoxybenzamide 
• 83-30-7 acide 2,4,6-trihydroxybenzoique 
• 14615-72-6 3,5-dibenzyloxybenzaldehyde 
• 529-56-6 sphaerophorin 
• 4762-26-9 hexyltriphenylphosphonium bromide 
• 524-14-1 S-(hydrogen malonyl)coenzyme A 
• 1264-52-4 octanoyl coenzyme A 
• 1020408-63-2 C₃₉H₅₈O₁₅ 

Downstream Products

• 83375-19-3 2,6-dihydroxy-4-heptylacetophenone 
• 83375-18-2 2,4-dihydroxy-6-heptylacetophenone 
• 55824-13-0 5-heptyl-2-((1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-enyl)benzene-1,3-diol 
• 529-56-6 sphaerophorin 
• 124-07-2 Octanoic acid 
• 855875-36-4 2-heptyl-4,6-dihydroxy-benzaldehyde 
• 4670-13-7 2-hydroxy-4-methoxy-6-heptylacetophenone 
• 4670-14-8 siphulin trimethyl ether 
• 137571-94-9 ent-KS-501 
• 120634-86-8 KS-501 
• 137571-92-7 3'-(benzyloxy)-6'-<<5''-(1-heptyl)-3''-hydroxyphenoxy>carbonyl>-5'-(1-heptyn-1-yl)phenyl 2,3-di-O-benzyl-L-galactofuranoside 
• 137571-84-7 3'-(benzyloxy)-6'-<<5''-(1-heptyl)-3''-hydroxyphenoxy>carbonyl>-5'-(1-heptyn-1-yl)phenyl 2,3-di-O-benzyl-D-galactofuranoside 

Relevant articles and documents

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