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CAS No. : | 136-77-6 | MDL No. : | MFCD00002284 |
Formula : | C12H18O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WFJIVOKAWHGMBH-UHFFFAOYSA-N |
M.W : | 194.27 | Pubchem ID : | 3610 |
Synonyms : |
4-Hexylresorcinol;NSC 1570;Ascaryl;Ascarinol;Ascaricid;p-Hexylresorcinol;4-n-Hexylresorcinol
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 59.49 |
TPSA : | 40.46 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.04 cm/s |
Log Po/w (iLOGP) : | 2.5 |
Log Po/w (XLOGP3) : | 3.45 |
Log Po/w (WLOGP) : | 3.22 |
Log Po/w (MLOGP) : | 2.67 |
Log Po/w (SILICOS-IT) : | 3.08 |
Consensus Log Po/w : | 2.99 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.21 |
Solubility : | 0.121 mg/ml ; 0.000624 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.98 |
Solubility : | 0.0203 mg/ml ; 0.000104 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.66 |
Solubility : | 0.0423 mg/ml ; 0.000218 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.73 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86.2% | With palladium 10% on activated carbon; hydrogen In methanol at 80℃; Autoclave | In a 1.0 L autoclave, 104.1 g (0.5 mol) of 4-hexanoylresorcinol was added.Add 500ml of methanol,10percent wet Pd/C (20.0 g),Heated to 80 °C,Hydrogen gas was introduced at a pressure of 1.5 MPa and the GC was followed until the end of the reaction.The reaction solution was filtered to recover Pd/C, and the filtrate was concentrated to a light brown-red oily liquid.Recrystallization from dichloromethane and n-hexane gave 83.7 g of 4-hexyl resorcinol,GC>99.0percent, yield 86.2percent, total yield 77.5percent over two steps. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86.2% | With palladium 10% on activated carbon; hydrogen; In methanol; at 80℃; under 11251.1 Torr;Autoclave; | In a 1.0 L autoclave, 104.1 g (0.5 mol) of 4-hexanoylresorcinol was added.Add 500ml of methanol,10% wet Pd/C (20.0 g),Heated to 80 C,Hydrogen gas was introduced at a pressure of 1.5 MPa and the GC was followed until the end of the reaction.The reaction solution was filtered to recover Pd/C, and the filtrate was concentrated to a light brown-red oily liquid.Recrystallization from dichloromethane and n-hexane gave 83.7 g of 4-hexyl resorcinol,GC>99.0%, yield 86.2%, total yield 77.5% over two steps. |
With hydrogen;nickel; In methanol; at 70 - 95℃; under 7500.75 - 37503.8 Torr;Product distribution / selectivity; | 85 g 4-caproylresorcinol is dissolved in 770 mL of MeOH. 25 g Ni-catalyst are added and the mixture is hydrogenated at 70 C. and 10 bar. The GC quality of the crude material is 94%. The catalyst is filtered off, most of the MeOH is distilled off, 350 mL of toluene are added and the mixture is distilled until the head temperature indicates full removal of the MeOH. The mixture is cooled to room temperature, and the product is filtered off and dried.; 85 g 4-caproylresorcinol (derived from the Example 5, HF-process) is dissolved in 255 mL of MeOH. 10 g Ni-catalyst are added and the mixture is hydrogenated at 80-95 C. and 30-50 bar. The GC quality of the crude material is only 86%. The catalyst is filtered off, most of the MeOH is distilled off, 350 mL of toluene are added and the mixture is distilled until the head temperature indicates full removal of the MeOH. The mixture is cooled to room temperature, and the product is filtered off and dried. | |
With hydrogenchloride; zinc; In ethanol; water;Heating / reflux; | Given the known sensitivity issues associated with commercial grade hexylresorcinol, evaluation of the skin sensitivity to the purified hexylresorcinol was also evaluated. Skin sensitivity was evaluated following the method cited in the reference Appraisal of the Safety of Chemicals in Food, Drugs and Cosmetics, published by The <n="21"/>Association of Food and Drug Officials of The United States. The specific method employed used nine inductive patchings, not the ten cited in the reference, under occlusive patch conditions.[0059] Highly pure hexylresorcinol was prepared as follows: A mixture comprising 40 grams hexanoic acid, 6.0 grams zinc chloride and 30 ml of xylene was heated to reflux. 10 grams of resorcinol was gradually added to the foregoing and mixture allowed to reflux for 4 to 6 hours. Water formed during the reaction was removed by the addition of xylene through azeotropic distillation. Thereafter, the reaction mixture was poured into 100 ml of water and the organic layer separated. The separated organic layer was then subjected to fractional distillation to recover the solvent, hexanoic acid and the 4-hexanoylresorcinol. The distilled product was then crystallized from hexane to yield approximately 15 grams crude hexanoylresorcinol. 15 grams hexanoylresorcinol was then dissolved in 30 ml of ethanol and treated with 18 grams of activated zinc and 60 ml of 25% hydrochloric acid at mild reflux. After completion of the reaction the ethanol is removed and the reaction mixture is extracted with toluene. The organic layer is washed with water (30 ml - 2 times) and concentrated to dryness to give a crude hexylresorcinol (yield 13gm). This on crystallization from hexane gave 10 grams of hexylresorcinol having resorcinol content of 0.005% to nil.[0060] Samples were prepared for evaluation by diluting the highly pure hexylresorcinol in corn oil to a 5% concentration, with dilutions freshly prepared on each application day. 0.2 ml of the diluted test material was dispensed onto occlusive, hypoallergenic patches and the treated patches applied directly to the skin of the infrascapular regions of the back, to the right or left of the midline of each subject: one hundred and eleven subjects were employed. After application of the patch, each subject was dismissed with instructions not to wet or expose the test area to direct sunlight. The patch was removed by the subject after 24 hours. This procedure was repeated every Monday, Wednesday and Friday for three consecutive weeks until a series of nine consecutive 24 hour exposures had been made. During the test period, the test area on the subjects' backs were observed for evidence of edema or erythema just before applications two through nine and the next test date following application nine. If evidence of a reaction was found, the area of edema and/or erythema was then measured and recorded: edema being estimated by an evaluation of the skin with respect to the contour of the <n="22"/>unaffected normal skin. The subjects were then given a 10 - 14 day rest period after which a challenge or retest patch saturated with 0.2 ml of the hexylresorcinol dilutions was applied to a previously unexposed test site. The challenge or retest sites were monitored and scored 24 and 48 hours after application. Based on the test results, the 5% dilution in corn oil of the purified hexylresorcinol was determined to be a NON-PRIMARY IRRITANT and a NON-PRIMARY SENSITIZER according to the reference. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | 5-hexyl-2,4-dihydroxybenzaldehyde (2). POC13 (72 mL) was added to the freshly distilled DMF (90 mL) at -5 C. The reaction mixture was stirred for 1 hr followed by addition of hexylresorcinoi (104 g). The reaction mixture was stirred at room temperature for 12 hr. A 30% solution of sodium acetate (500 mL) and ice (1000 mL) were added. The solid product was filtered off and re-crystallized from ethanol to give compound 2 in 73% yield (87.5 g). m.p. 112 C. | |
73% | 5-hexyl-2,4-dihydroxybenzaldehyde (2) POCl3 (72 mL) was added to the freshly distilled DMF (90 mL) at -5 C. The reaction mixture was stirred for 1 hr followed by addition of hexylresorcinol (104 g). The reaction mixture was stirred at room temperature for 12 hr. A 30% solution of sodium acetate (500 mL) and ice (1000 mL) were added. The solid product was filtered off and re-crystallized from ethanol to give compound 2 in 73% yield (87.5 g). m.p. 112 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The other portion was dehydrogenated using a palladium/carbon catalyst (0.2 g palladium on 1.8 grams of carbon carrier) under the aforesaid conditions whereby 25.9 grams(~ 88 % yield) of 4-n-hexyl-resorcinol were obtained. |
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
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Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
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P402 | Store in a dry place. |
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P422 | |
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P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
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Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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