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4-Hexylresorcinol

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Name

4-Hexylresorcinol

EINECS 205-257-4
CAS No. 136-77-6 Density 1.049 g/cm3
PSA 40.46000 LogP 3.22060
Solubility 0.05 g/100 mL (18 °C) in water Melting Point 65-67 °C(lit.)
Formula C12H18O2 Boiling Point 329.5 °C at 760 mmHg
Molecular Weight 194.274 Flash Point 155.2 °C
Transport Information N/A Appearance slightly red powder
Safety 22-36/37/38-20/21/22 Risk Codes 22-36/37/38-20/21/22
Molecular Structure Molecular Structure of 136-77-6 (4-Hexyl-1,3-benzenediol) Hazard Symbols HarmfulXn
Synonyms

Resorcinol,4-hexyl- (8CI);1,3-Dihydroxy-4-hexylbenzene;4-(1-Hexyl)resorcinol;4-Hexyl-1,3-dihydroxybenzene;4-Hexylresorcine;4-Hexylresorcinol;4-n-Hexylresorcinol;Adrover;Antascarin;Ascaricid;Ascarinol;Ascaryl;

Article Data 15

4-Hexylresorcinol Synthetic route

3144-54-5

4-hexanoylresorcinol

136-77-6

4-Hexylresorcinol

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 80℃; under 11251.1 Torr; Reagent/catalyst; Autoclave;86.2%
With hydrogenchloride; amalgamated zinc In ethanol67%
With hydrogenchloride; amalgamated zinc In ethanol; water Heating;

4-hex-2-enyl-resorcinol

136-77-6

4-Hexylresorcinol

Conditions
ConditionsYield
With ethanol; platinum Hydrogenation;
4-caproyl-resorcinol

4-caproyl-resorcinol

136-77-6

4-Hexylresorcinol

Conditions
ConditionsYield
With hydrogenchloride; amalgamated zinc
With hydrogenchloride; amalgamated zinc
142-61-0

Hexanoyl chloride

136-77-6

4-Hexylresorcinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aluminum chloride / nitrobenzene / cooling
2: zinc amalgamate; conc. hydrochloric acid / ethanol; H2O / Heating
View Scheme
Multi-step reaction with 2 steps
1: 68 percent / aluminum chloride / nitrobenzene
2: 67 percent / zinc amalgame, hydrochloric acid / ethanol
View Scheme
108-46-3

recorcinol

diazotized. 2.5-diamino-p-cymene

diazotized. 2.5-diamino-p-cymene

136-77-6

4-Hexylresorcinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aluminum chloride / nitrobenzene / cooling
2: zinc amalgamate; conc. hydrochloric acid / ethanol; H2O / Heating
View Scheme
108-46-3

recorcinol

acid

acid

136-77-6

4-Hexylresorcinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 68 percent / aluminum chloride / nitrobenzene
2: 67 percent / zinc amalgame, hydrochloric acid / ethanol
View Scheme
34686-76-5

1-bromo-2-hexene

136-77-6

4-Hexylresorcinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K2CO3; acetone
2: ethanol; platinum / Hydrogenation
View Scheme
108-46-3

recorcinol

136-77-6

4-Hexylresorcinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K2CO3; acetone
2: ethanol; platinum / Hydrogenation
View Scheme
Multi-step reaction with 2 steps
1: zinc(II) chloride / 6 h / 95 - 100 °C
2: zinc; hydrogenchloride / ethanol
View Scheme
95-48-7

ortho-cresol

108-46-3

recorcinol

111-27-3

hexan-1-ol

136-77-6

4-Hexylresorcinol

Conditions
ConditionsYield
With sulfuric acid In di-isopropyl ether
142-62-1

hexanoic acid

136-77-6

4-Hexylresorcinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: zinc(II) chloride / 6 h / 95 - 100 °C
2: zinc; hydrogenchloride / ethanol
View Scheme

4-Hexylresorcinol Chemical Properties


IUPAC Name: 4-Hexylbenzene-1,3-diol
Molecular Weight: 194.27012 [g/mol]
Molecular Formula: C12H18O2
XLogP3: 3.5
H-Bond Donor: 2
H-Bond Acceptor: 2 
EINECS: 205-257-4
Product Categories: Miscellaneous 
Solubility: chloroform: 50 mg/mL, clear
Water Solubility: 0.05 g/100 mL (18 ºC) 
Stability: Stable. Incompatible with acid chlorides, acid anhydrides, oxidizing agents. 
Index of Refraction: 1.54
Molar Refractivity: 58.09 cm3
Molar Volume: 185.1 cm3
Surface Tension: 42.6 dyne/cm
Density: 1.049 g/cm3
Flash Point: 155.2 °C
Enthalpy of Vaporization: 59.47 kJ/mol
Boiling Point: 329.5 °C at 760 mmHg
Vapour Pressure: 9.25E-05 mmHg at 25 °C
Appearance: slightly red powder
Melting Point: 65-67 °C(lit.)
Classification Code of 4-Hexylresorcinol (CAS NO.136-77-6): Anthelmintic; Anthelmintics; Anti-Infective Agents; Antiparasitic Agents; Drug / Therapeutic Agent; Mutation data; Reproductive Effect; Skin / Eye Irritant; Tumor data

4-Hexylresorcinol Uses

 4-Hexylresorcinol (CAS NO.136-77-6) is used as an antiseptic, commonly employed in a dilution of 1:1000. It commonly can be used  on small skin infections, or as an ingredient in throat lozenges. It has the same lightening effect as 2% hydroquinone over an 8 week period in vivo studies conducted on Synovea HR 4-Hexylresorcinol.

4-Hexylresorcinol Production

In the manutacture of 4-Hexylresorcinol (CAS NO.136-77-6), resorcinol and caproic acid are heated with a condensing agent, such as zinc chloride, and the intermediate ketone derivative is formed, which is purified by vacuum distillation. After reduction with zinc amalgam and hydrochloric acid, impure 4-Hexylresorcinol is formed, which can be purified by vacuum distillation.

4-Hexylresorcinol Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LDLo oral 400mg/kg (400mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 28, Pg. 609, 1931.
mouse LD50 intraperitoneal 335mg/kg (335mg/kg)   Japanese Kokai Tokyo Koho Patents. Vol. #90-292213,
mouse LD50 oral 1040mg/kg (1040mg/kg)   Pharmazie. Vol. 30, Pg. 147, 1975.
mouse LDLo subcutaneous 750mg/kg (750mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 148, 1959.
mouse LDLo unreported 100mg/kg (100mg/kg)   Annals of Tropical Medicine and Parasitology. Vol. 32, Pg. 177, 1938.
rat LD50 oral 550mg/kg (550mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 53, Pg. 198, 1935.

4-Hexylresorcinol Consensus Reports

Reported in EPA TSCA Inventory.

4-Hexylresorcinol Safety Profile

A poison by ingestion and intraperitoneal routes. Moderately toxic by subcutaneous route. Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. An eye irritant. Concentrated solutions can cause burns on the skin and mucous membranes in humans. An anthelmintic and topical antiseptic. When heated to decomposition it emits acrid smoke and fumes.
Hazard Codes:  Xn
Risk Statements:  22-36/37/38-20/21/22
22:  Harmful if swallowed 
36/37/38:  Irritating to eyes, respiratory system and skin
20/21/22:  Harmful by inhalation, in contact with skin and if swallowed
Safety Statements:  26-36-24/25
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:  Wear suitable protective clothing 
24/25:  Avoid contact with skin and eyes
WGK Germany:  3
RTECS:  VH1575000

4-Hexylresorcinol Specification

 4-Hexylresorcinol (CAS NO.136-77-6), its Synonyms are 1,3-Dihydroxy-4-hexylbenzene ; 1,3-Dihydroxy-4-n-hexylbenzene ; 4-(1-Hexyl)resorcinol ; 4-Hexyl-1,3-benzenediol ; 4-Hexyl-1,3-dihydroxybenzene ; 4-Hexylresorcine ; 4-4-Hexylresorcinol ; 4-n-4-Hexylresorcinol ; Crystoids ; Cystoids anthelmintic ; Worm-agen ; p-4-Hexylresorcinol .

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