| Identification | More | [Name]
Isophorone | [CAS]
78-59-1 | [Synonyms]
3,5,5-TIMETHYL-2-CYCLOHEXEN-1-ONE
3,5,5-TRIMETHYL-2-CYCLOHEXEN-1-ONE
3,5,5-TRIMETHYL-2-CYCLOHEXENE-1-ONE
3,5,5-TRIMETHYL-2-CYCLOHEXENONE
3,5,5-TRIMETHYL-CYCLOHEX-2-ENONE
3,5,5-TRIMETHYLCYCLOHEXEN-1-ONE
3,5,5-TRIMETHYL CYCLOHEXENE-2-ONE
FEMA 3553
ISOPHORONE
1,1,3-Trimethyl-3-cyclohexene-5-one
2-cyclohexen-1-one,3,5,5-trimethyl-
3,3,5-Trimethyl-2-cyclohexen-1-one
3,3,5-trimethyl-5-cyclohexen-1-one
3,5,5-Tirmethyl-2-cyclohexen-1-one
3,5,5-Trimethyl-2-cyclohexen-1-on
3,5,5-trimethyl-2-cyclohexen-1-on(german,dutch)
3,5,5-trimethylcyclohex-2-en-1-one
3,5,5-trimethylcyclohex-2-ene-1-one
3,5,5-Trimethylcyclohexen-2-one-1
3,5,5-Trimetil-2-cicloesen-1-one | [EINECS(EC#)]
201-126-0 | [Molecular Formula]
C9H14O | [MDL Number]
MFCD00001584 | [Molecular Weight]
138.21 | [MOL File]
78-59-1.mol |
| Chemical Properties | Back Directory | [Appearance]
light yellow liquid | [Melting point ]
-8 °C (lit.) | [Boiling point ]
213-214 °C (lit.) | [density ]
0.923 g/mL at 25 °C(lit.)
| [vapor density ]
4.77 (vs air)
| [vapor pressure ]
0.2 mm Hg ( 20 °C)
| [FEMA ]
3553 | [refractive index ]
n20/D 1.476(lit.)
| [Fp ]
184 °F
| [storage temp. ]
2-8°C | [solubility ]
14.5g/l | [form ]
Liquid | [color ]
Clear colorless to yellow | [Odor]
Like camphor. | [Stability:]
Stable. Substances to be avoided include strong bases, strong acids and strong oxidizing agents. | [explosive limit]
0.8-3.8%(V) | [Odor Type]
woody | [Water Solubility ]
Soluble in water (12g/L). | [JECFA Number]
1112 | [Merck ]
14,5196 | [BRN ]
1280721 | [Henry's Law Constant]
(x 10-6 atm?m3/mol):
5.8 (calculated, U.S. EPA, 1980a) | [Exposure limits]
TLV-TWA 25 mg/m3 (5 ppm); IDLH 800
ppm. | [LogP]
1.67-1.7 at 20℃ | [CAS DataBase Reference]
78-59-1(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Cyclohexen-1-one, 3,5,5-trimethyl-(78-59-1) | [EPA Substance Registry System]
78-59-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R21/22:Harmful in contact with skin and if swallowed .
R36/37:Irritating to eyes and respiratory system .
R40:Limited evidence of a carcinogenic effect. | [Safety Statements ]
S13:Keep away from food, drink and animal feeding stuffs .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S46:If swallowed, seek medical advice immediately and show this container or label . | [RIDADR ]
UN 3082 9 / PGIII | [WGK Germany ]
1
| [RTECS ]
GW7700000
| [Autoignition Temperature]
864 °F | [TSCA ]
Yes | [HS Code ]
29142990 | [Hazardous Substances Data]
78-59-1(Hazardous Substances Data) | [Toxicity]
LD50 in male, female rats and male mice (mg/kg): 2700 ±200, 2100 ±200, 2200 ±200 orally (PB90-180225) | [IDLA]
200 ppm |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Acetone-->4-Penten-2-one, 4-methyl--->Methyl acetoacetate-->Diacetone Alcohol-->Mesityl oxide | [Preparation Products]
Isophorone diisocyanate-->Cyclohexanone, 3,3,5-trimethyl-, (5S)--->3,5,5-trimethylcyclohex-3-en-1-one-->2,2,4,4,6-pentamethyl-hexahydropyrimidine-->ISOPHORONE (3-METHYL-D3, 2,4,4,6,6-D5) |
| Hazard Information | Back Directory | [General Description]
A clear colorless liquid, with a camphor-like odor. Less dense than water and insoluble in water. Boiling point 420°F. Flash point near 200°F. Contact irritates skin and eyes. Toxic by ingestion. Used as a solvent and in pesticides. | [Reactivity Profile]
Ketones, such as ISOPHORONE(78-59-1), are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4. Forms explosive peroxides | [Air & Water Reactions]
Insoluble in water. | [Hazard]
Irritant to skin and eyes. Possible carcinogen. | [Health Hazard]
LIQUID: Irritating to skin and eyes. Harmful if swallowed. | [Fire Hazard]
Combustible. | [Physical properties]
Clear, colorless liquid with a sharp peppermint or camphor-like odor. Experimentally determined
detection and recognition odor threshold concentrations were 1.1 mg/m3 (190 ppbv) and 3.0 μg/m3
(530 ppbv), respectively (Hellman and Small, 1974). | [Occurrence]
Reported found in Burley tobacco, cranberry, macadamia nuts, peas, roasted filbert, saffron, wine, osmanthus,
grapefruit juice, papaya, kohlrabi, Parmesan cheese, roast beef, black tea, oats, Japanese plum, prunes, plumcot, starfruit, mango,
rice, buckwheat, okra and sweet grass oil. | [Uses]
Isophorone is used as a solvent for vinylresins and cellulose esters, and in pesticides. | [Uses]
Solvent for lacquers, resins, and
plastics | [Uses]
Solvent in some printing inks, paints, lacquers and adhesives. | [Definition]
ChEBI: A cyclic ketone, the structure of which is that of cyclohex-2-en-1-one substituted by methyl groups at positions 3, 5 and 5. | [Preparation]
Isophorone is produced on a multi-thousand ton scale by the aldol condensation of acetone using KOH. Diacetone alcohol, mesityl oxide, and 3-hydroxy-3,5,5-trimethylcyclohexan-1-one are intermediates. A side product is beta-isophorone, where the C=C group is not conjugated with the ketone. | [Aroma threshold values]
Detection: 0.20 ppm; aroma characteristics at 1.0%: cooling, woody, camphoraceous, slightly green and
herbal | [Taste threshold values]
Taste characteristics at 30 ppm: sweet, green, waxy, pungent camphoreous, cooling minty | [Synthesis Reference(s)]
Synthetic Communications, 22, p. 1845, 1992 DOI: 10.1080/00397919208021315
Synthesis, p. 905, 1978 DOI: 10.1055/s-1978-24936 | [Flammability and Explosibility]
Notclassified | [Chemical Reactivity]
Reactivity with Water No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent. | [Industrial uses]
Isophorone is an excellent solvent for cellulose esters, nitrocellulose, natural and synthetic resins. Isophorone has a very high aromatic hydrocarbon dilution ratio in nitrocellulose formulations: 5.7 for toluene and 5.1 for xylene. The excellent solvency of isophorone allows the preparation of 45% solids nitrocellulose solutions at room temperatures. | [Biochem/physiol Actions]
Taste at 30 ppm | [Synthesis]
Isophorone is an intermediate in the synthesis of 3,5-xylenol, 3,3,5-trimethylcyclohexanol | [Carcinogenicity]
In a 2 year bioassay in rats and
mice (conducted by gavage on a 5- day/week treatment
schedule) at dose levels of 0, 250, and 500 mg/kg/day isophorone, there was decreased survival of male rats and
slight nephrotoxicity in female rats. There was no evidence
of carcinogenicity in female rats or mice. In male rats, there
was an increase in renal tumors in animals given either 250
or 500 mg/kg/day, and a low incidence of preputial gland
tumors at 500 mg/kg. Other proliferative lesions in male rats
included hyperplasia of the renal pelvis and tubular cell
hyperplasia. | [Environmental Fate]
Biological. The pure culture Aspergillus niger biodegraded isophorone to 3,5,5-trimethyl-2-
cyclo-hexene-1,4-dione, 3,5,5-trimethylcyclohexane-1,4-dione, (S)-4-hydroxy-3,5,5-trimethyl-2-
cyclohex-1-one, and 3-hydroxymethyl-5,5-dimethyl-2-cyclohexen-1-one (Mikami et al., 1981).
Chemical/Physical. At an influent concentration of 1,000 mg/L, treatment with GAC resulted in
an effluent concentration of 34 mg/L. The adsorbability of the carbon used was 193 mg/g carbon
(Guisti et al., 1974).
Isophorone will not hydrolyze in water.
At influent concentrations of 10, 1.0, 0.1, and 0.001 mg/L, the GAC adsorption capacities were
78.3, 32.0, 13.1, and 5.4 mg/g, respectively (Dobbs and Cohen, 1980). | [Purification Methods]
Wash isophorone with aqueous 5% Na2CO3 and then distil it under reduced pressure immediately before use. Alternatively, it can be purified via the semicarbazone. [Erskine & Waight J Chem Soc 3425 1960, Beilstein 7 IV 165.] | [Toxicity evaluation]
The toxicological mechanisms of isophorone are not well
characterized. Critical effects include irritation, narcosis,
malaise, fatigue, and CNS depression. Isophorone may induce
its neurological effects by interference with neuronal impulse
transmissions via physical interaction with nerve membrane
components. In animal models, isophorone may also act by
inducing neuropathy, involving binding to globulin proteins,
although this mechanism may not be relevant to humans.
Lesions of the liver have been observed after overexposure in
mouse models, although it is not clear whether isophorone
elicited the lesions directly or by enhancing an age-related
process. DNA-binding studies in mice have shown no significant
covalent binding of isophorone or its metabolites to DNA
from liver or kidney cells, supporting a potential nongenotoxic
mechanism of toxicity. | [Waste Disposal]
Incineration. |
| Questions And Answer | Back Directory | [Description]
Isophorone (chemical formula: C9H14O) has its full name being 3, 5, 5-Trimethyl-2-cyclohexen-1-one. It is a kind of α, β-unsaturated cyclic ketone, and is a flavoring ingredient existing in cranberries and saffron. Isophorone can be used as a solvent in some printing inks, paints, lacquers, adhesives, copolymers, coatings, finishings and pesticide. It can also act as an intermediate in organic synthesis as well as the ingredient in wood preservatives and floor sealants. It is mainly manufactured through the self-condensation of acetone with KOH.
| [Chemical Properties]
Isophorone, an alpha, beta-unsaturated ketone, is also an industrial solvent used in a variety of different applications. Most of the isophorone used in industry is used in vinyl coatings and inks.
Isophorone is an insoluble, colorless to white liquid and has an odor similar to peppermint. Its characteristic odor is detectable at concentrations as low as 1.00 mg/m3 (0.2 ppm) (Ruth, 1986). Although not highly volatile, with a vapor pressure of 0.438mm Hg at 25 °C.
| [References]
https://en.wikipedia.org/wiki/Isophorone
https://pubchem.ncbi.nlm.nih.gov/compound/isophorone#section=Top
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