Para Cymene

Product Name:

Para Cymene

Synonyms:

4-CYMENE;4-METHYLISOPROPYLBENZENE;4-ISOPROPYLTOLUENE;lsopropyltoluene;1-(1-methylethyl)-4-methylbenzene;1-isopropyl-4-methyl-benzen;1-methyl-4-(1-methylethyl)-benzen;1-methyl-4-(1-methylethyl)benzene

CAS:

99-87-6

MF:

C10H14

MW:

134.22

EINECS:

202-796-7

Product Categories:

Artemisia vulgaris;Boswellia carterii;Building Blocks;Carthamus tinctorius (Safflower oil);Chamaemelum nobile (Chamomile tea);Chemical Synthesis;Citrus aurantium (Seville orange);Curcuma longa (Turmeric);Elettaria Cardamomum (Cardamom);Ginkgo biloba;Humulus lupulus (Hops);Hypericum perforatum (St John′;Lavandula angustifolia (Lavendar tea);Melaleuca alternifolia;Nutrition Research;Ocimum basilicum (Basil);Organic Building Blocks;Phytochemicals by Plant (Food/Spice/Herb);s wort);Zingiber officinale (Ginger);Analytical Chemistry;Standard Solution of Volatile Organic Compounds for Water & Soil Analysis;Standard Solutions (VOC);Arenes

Mol File:

99-87-6.mol

Melting point 

-68 °C

Boiling point 

176-178 °C(lit.)

density 

0.86 g/mL at 25 °C(lit.)

vapor density 

4.62 (vs air)

vapor pressure 

1.5 mm Hg ( 20 °C)

FEMA 

2356 | P-CYMENE

refractive index 

n20/D 1.490(lit.)

Fp 

117 °F

storage temp. 

Flammables area

form 

Liquid

color 

Clear

Odor

Mild, pleasant; aromatic, solvent-type.

Odor Threshold

0.057ppm

explosive limit

5.6%

Water Solubility 

PRACTICALLY INSOLUBLE

JECFA Number

1325

Merck 

14,2763

BRN 

1903377

Stability:

Stable. Flammable. Incompatible with strong oxidizing agents, strong acids, strong bases.

InChIKey

HFPZCAJZSCWRBC-UHFFFAOYSA-N

CAS DataBase Reference

99-87-6(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1-methyl-4-(1-methylethyl)-(99-87-6)

EPA Substance Registry System

p-Cymene (99-87-6)

Hazard Codes 

Xi

Risk Statements 

10-36/37/38

Safety Statements 

26-36

RIDADR 

UN 2046 3/PG 3

WGK Germany 

2

RTECS 

GZ5950000

Autoignition Temperature

817 °F

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29029090

Hazardous Substances Data

99-87-6(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 4750 mg/kg (Jenner)

Chemical Properties

p-Cymene has a citrusy aroma reminiscent of lemon. It is colorless liquid with a strong, characteristic odor reminiscent of carrot. It tends to darken with aging. It occurs naturally in orange peel oil, mandarin peel oil, satsuma mandarin peel oil, coldpressed lime peel oil, distilled lime peel oil, cinnamon leaf, etc. 4-isopropyltoluene has antimicrobial properties. It is used as a flavor ingredient permitted for direct addition to food for human consumption.

Uses

p-Cymene is an alkyl aromatic hydrocarbon mainly used to study oxidation reactions under various conditions to synthesize highly valuable intermediates and building-blocks such as cymene hydroperoxide, 4-methyl acetophenone, 4-isopropyl benzyl alcohol, 4-isopropyl benzaldehyde and 4-isopropyl benzoic acid etc.
Medicinally, p-cymene is used to prevent coughs and eliminate phlegm as well as being a flavouring agent, and being used in the production of fungicides and pesticides. It is considered to be “generally recognised as safe” (GRAS) by the U.S. Food and Drug Administration. Its potential in the prevention of protein glycation mediated diabetic complications has also been confirmed, and it has been suggested as an in vivo antioxidant compound due to its ability to reduce the formation of oxygen and nitrogen reactive species, acting as a potential neuroprotective agent in the brain. Therefore, it could be involved in the treatment of oxidative stress related diseases.

Production Methods

p-cymene is conventionally produced by the Friedel-Crafts alkylation of toluene with isopropanol, or of benzene with methyl or isopropyl halides.

References

[1] George A. Burdock, Encyclopedia of Food and Color Additives, Volume 1, 1996
[2] C.F. Bagamboula, M. Uyttendaele and J. Debevere, Inhibitory effect of thyme and basil essential oils, carvacrol, thymol, estragol, linalool and p-cymene towards Shigella sonnei and S. flexneri, Food Microbiology, 2004, vol. 21, 33-42

Chemical Properties

p-Cymene is a monoterpene that is found in a variety of plants, including C. sativa, and has diverse biological activities, including antimicrobial, anticancer, antioxidant, anti-inflammatory, antinociceptive, and anxiolytic properties.p-Cymene inhibits the growth of S. typhimurium, E. coli, L. monocytogenes, S. epidermidis, and S. aureus with MIC values ranging from 0.266 to 0.608% v/v.It decreases the invasive activity of HT-1080 human fibrosarcoma cells in vitro by 87% when used at a concentration of 600 μM.In mouse hippocampus, p-Cymene (50 mg/kg, i.p.) reduces lipid peroxidation and nitrite content by 65.5 and 71.2%, respectively, and increases superoxide dismutase (SOD) and catalase activities by 22.7 and 119.3%, respectively, compared to vehicle control animals.Formulations containing p-cymene have been used as flavoring agents.

Preparation

Obtained chiefly from the wash water of sulfite paper.

Definition

ChEBI: A monoterpene that is toluene substituted by an isopropyl group at position 4.

Aroma threshold values

Aroma characteristics at 1% EtoH: harsh chemical, woody and terpy-like with an oxidized citrus lemon note. It has spicy nuances reminiscent of cumin, oregano and cilantro

Taste threshold values

Taste characteristics at 1 to 10 ppm: terpy and rancid with slightly woody, oxidized citrus notes. It has spice nuances of green pepper and oregano.

General Description

Colorless liquid with a mild pleasant odor. Floats on water.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as CYMENE, and strong oxidizing agents. They can react exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction.

Health Hazard

Inhalation causes impairment of coordination, headache. Contact with liquid causes mild irritation of eyes and skin. Ingestion causes irritation of mouth and stomach.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Chemical Reactivity

Reactivity with Water: No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Safety Profile

Mildly toxic by ingestion. Humans sustain central nervous system effects at low doses. A skin irritant. Flammable liquid. Explosion Hazard: Slight in the form of vapor. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and fumes.

Purification Methods

Wash p-cymene with cold, conc H2SO4 until there is no further colour change, then repeatedly with H2O, 10% aqueous Na2CO3 and H2O again. Dry it over Na2SO4, CaCl2 or MgSO4, and distil it. Further purification steps include steam distillation from 3% NaOH, percolation through silica gel or activated alumina, and a preliminary reflux for several days over powdered sulfur. Store it over CaH2. [Beilstein 5 IV 1060.]

Raw materials

(+)-Dipentene-->Cineole

Preparation Products

Acetone-->m-Cresol-->Cresol-->p-Toluic acid-->Isoproturon-->4-Bromomethylbenzoic acid-->4-Isopropylbenzaldehyde-->GAMMA-TERPINENE-->2-NITRO-4-CYMENE