Cresol
Cresols are organic compounds which are methylphenols. They are a widely occurring natural and manufactured group of aromatic organic compounds which are categorized as phenols (sometimes called phenolics). Depending on the temperature, cresols can be solid or liquid because they have melting points not far from room temperature. Like other types of phenols, they are slowly oxidized by long exposure to air and the impurities often give cresols a yellowish to brownish red tint. Cresols have an odor characteristic to that of other simple phenols, reminiscent to some of a "medicine" smell.
Chemical structure
In its chemical structure, a cresol molecule has a methyl group substituted onto the benzene ring of a phenol molecule. There are three forms of cresols with formula (CH3)C6H4(OH) that are only slightly different in their chemical structure: ortho-cresol (o-cresol), meta-cresol (m-cresol), and para-cresol (p-cresol). These forms occur separately or as a mixture.
| Template:Chembox header align="center" colspan="4" | Isomers of Cresol | ||||
|---|---|---|---|---|
| Template:Chembox header align="center" colspan="4" | General | ||||
| Common name | o-cresol | m-cresol | p-cresol | |
| Systematic name | 2-methylphenol | 3-methylphenol | 4-methylphenol | |
| Other names | ortho-cresol | meta-cresol | para-cresol, 4-Hydroxytoluene | |
| Molecular formula | C7H8O | |||
| SMILES | Oc1c(C)cccc1 | Oc1cc(C)ccc1 | Oc1ccc(C)cc1 | |
| Molar mass | 108.14 g/mol | |||
| Appearance at room temperature and pressure |
greasy-looking solid ready to melt on hot day |
thicker liquid | greasy-looking solid | |
| CAS number | [95-48-7] | [108-39-4] | [106-44-5] | |
| CAS number for mixture of cresols [1319-77-3] | ||||
| Template:Chembox header align="center" colspan="4" | Properties | ||||
| Density and phase | 1.05 g/cm3, liquid | 1.03 g/cm3, liquid | 1.02 g/cm3, liquid | |
| Solubility in pure water at 20-25°C |
2.5 g/100 ml | 2.4 g/100 ml | 1.9 g/100 ml | |
| soluble in strongly alkaline water | ||||
| Melting point | 29.8 °C (303.0 K) | 11.8 °C (285.0 K) | 35.5 °C (309.7 K) | |
| Boiling point | 191.0 °C (464.2 K) | 202.0 °C (475.2 K) | 201.9 °C (475.1 K) | |
| Acidity (pKa) | 10.26 | 10.99 | 10.26 | |
| Viscosity | solid at 25 °C | ? cP at 25 °C | solid at 25 °C | |
| Template:Chembox header align="center" colspan="4" | Structure | ||||
| Molecular shape | ? | ? | ? | |
| Coordination geometry | ? | |||
| Crystal structure | ? | |||
| Dipole moment | ? D | ? D | ? D | |
| Template:Chembox header align="center" colspan="4" | Hazards | ||||
| MSDS | External MSDS | ? | ? | |
| Main hazards | flammable, ingestion and inhalation toxicity hazard | |||
| Flash point | 81°C c.c. | 86 °C | 86°C c.c. | |
| R/S statement | R: 24/25-34 S: (1/2-)36/37/39-45 | |||
| RTECS number | ? | ? | ? | |
| Template:Chembox header align="center" colspan="4" | Supplementary data page | ||||
| Structure & properties | n, εr, etc. | |||
| Thermodynamic data | Phase behaviour Solid, liquid, gas | |||
| Spectral data | UV, IR, NMR, MS | |||
| Template:Chembox header align="center" colspan="4" | Related compounds | ||||
| Related phenols | phenol, xylenols | |||
| Related compounds | ? | |||
| Template:Chembox header align="center" colspan="4" | Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references | ||||
Applications
Cresols are used to dissolve other chemicals, as disinfectants and deodorizers, and to make specific chemicals that kill insect pests.
Cresol solutions are used as household cleaners and disinfectants, perhaps most famously under the trade name Lysol. In the past, cresol solutions have been used as antiseptics in surgery, but they have been largely displaced in this role by less toxic compounds. Lysol was also advertised as a disinfecting vaginal douche in mid-twentieth century America.
Cresols are found in many foods and in wood and tobacco smoke, crude oil, coal tar, and in brown mixtures such as creosote, cresolene and cresylic acids, which are wood preservatives. Small organisms in soil and water produce cresols when they break down materials in the environment.
Xylenols are dimethylphenols, or they can be thought of as methylcresols.
Health effects
Most exposures to cresols are at very low levels that are not harmful. When cresols are breathed, ingested, or applied to the skin at very high levels, they can be very harmful. Effects observed in people include irritation and burning of skin, eyes, mouth, and throat; abdominal pain and vomiting; heart damage; anemia; liver and kidney damage; facial paralysis; coma; and death.
Breathing high levels of cresols for a short time results in irritation of the nose and throat. Aside from these effects, very little is known about the effects of breathing cresols, for example, at lower levels over longer times.
Ingesting high levels results in kidney problems, mouth and throat burns, abdominal pain, vomiting, and effects on the blood and nervous system.
Skin contact with high levels of cresols can burn the skin and damage the kidneys, liver, blood, brain, and lungs.
Short-term and long-term studies with animals have shown similar effects from exposure to cresols. No human or animal studies have shown harmful effects from cresols on the ability to have children.
It is not known what the effects are from long-term ingestion or skin contact with low levels of cresols.