GAMMA-TERPINENE

GAMMA-TERPINENE Basic information
Product Name:GAMMA-TERPINENE
Synonyms:1-ISOPROPYL-4-METHYL-1,4-CYCLOHEXADIENE;1-ISOPROPYL-4-METHYL-1,4-CYCLOHEXADIENE P-MENTHA-1,4-DIENE;1,4-P-MENTHADIENE;GAMMA-TERPINENE;FEMA 3559;gamma-Terpinene solution;1,4-cyclohexadien, 1-methyl-4-(1-methylethyl)- [=gamma-terpinene];Chrithmene
CAS:99-85-4
MF:C10H16
MW:136.23
EINECS:202-794-6
Product Categories:Tri-Terpenoids;Biochemistry;Monocyclic Monoterpenes;Terpenes;Pyridines
Mol File:99-85-4.mol
GAMMA-TERPINENE Structure
GAMMA-TERPINENE Chemical Properties
Melting point -59.03°C (estimate)
Boiling point 182 °C (lit.)
density 0.85 g/mL at 25 °C (lit.)
vapor density 4.7 (vs air)
vapor pressure ~0.7 mm Hg ( 20 °C)
FEMA 3559 | P-MENTHA-1,4-DIENE
refractive index n20/D 1.474(lit.)
Fp 125 °F
storage temp. 2-8°C
solubility water: soluble5%, clear, colorless to faintly yellow
form Powder or Cyrstals
Specific Gravity0.849 (20/4℃)
color White
Odorat 10.00 % in dipropylene glycol. oily woody terpene lemon/lime tropical herbal
Odor Typeterpenic
Water Solubility 8.678mg/L(23.5 ºC)
Merck 14,9170
JECFA Number1340
BRN 2038347
Stability:Light Sensitive
InChIKeyYKFLAYDHMOASIY-UHFFFAOYSA-N
LogP5.4 at 25℃
CAS DataBase Reference99-85-4(CAS DataBase Reference)
EPA Substance Registry System.gamma.-Terpinene (99-85-4)
Safety Information
Hazard Codes Xi
Risk Statements 10-36/37/38
Safety Statements 26-36
RIDADR UN 2319 3/PG 3
WGK Germany 2
RTECS OS8070000
10-23
HazardClass 3.2
PackingGroup III
HS Code 29021990
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
GAMMA-TERPINENE Usage And Synthesis
Descriptionγ-Terpinene is a monoterpene that has been found in various plants, including C. sativa, with diverse biological activities. It scavenges 2,2''-diphenyl-1-picrylhydrazyl (DPPH; ) and 2,2''-azinobis(3-ethylbenzothiazoline-6-sulfonate) (ABTS+) free radicals (IC50s = 2.8 and 30 mM, respectively) and reduces hemolysis induced by AAPH in isolated human erythrocytes. γ-Terpinene reduces the growth of T. evansi in a concentration-dependent manner. It increases membrane permeability and decreases growth of X. oryzae bacteria. In vivo, γ-terpinene (100 mg/kg) reduces Triton WR1339-induced increases in serum cholesterol and triglyceride levels in rats. It reduces paw edema induced by histamine, bradykinin (Item No. 15539), carrageenan, and prostaglandin E2 (PGE2; ) in mice. It also inhibits fluid extravasation in a mouse model of acetic acid microvascular permeability and reduces neutrophil migration in lung in a mouse model of acute lung injury.
Chemical Propertiesclear liquid
Chemical Propertiesγ-Terpinene is a colorless liquid with an herbaceous citrus odor and can be prepared by isomerization of limonene.
Chemical Propertiesp-Mentha-1,4-diene has a characteristic lemon odor (not as lemony as the alpha-isomer, but warmer). It has a slightly bitter, herbaceous, citrus-like flavor; woody, terpene, tropical lemon odor.
OccurrenceReported found in papaya fruit, tea tree oil, tangerine, citrus, mandarins, Finocchoi fennel oil, papaya fruit, citrus peel oils, etc.
Usesγ–terpinene has been used as a standard in the determination of γ–terpinene, present in tea tree oil extracted from various parts of Melaleuca alternifolia tree and analyzed using gas chromatography coupled with mass spectrometry(GC-MS).
Usesγ-Terpinene can be used as:
  • Hydrogen precursor in the catalytic transfer hydrogenation of silyl enol ethers.
  • A reference compound in the kinetic study of ozonolysis of (E)-β-farnesene.
  • A hydrogen atom donor in the Cr-catalyzed radical cyclization of halo acetals.

DefinitionChEBI: Gamma-terpinene is one of three isomeric monoterpenes differing in the positions of their two double bonds (alpha- and beta-terpinene being the others). In gamma-terpinene the double bonds are at the 1- and 4-positions of the p-menthane skeleton. It has a role as an antioxidant, a plant metabolite, a volatile oil component and a human xenobiotic metabolite. It is a monoterpene and a cyclohexadiene.
PreparationFrom geranyl pyrophosphate by migration of a positive-charge, hydrid shift from the isopropyl side chain into the cyclohexenoid ring; from the essential oil of Lantana camara; also from p-cymene by the action of sodium and alcohol in liquid ammonia.
Taste threshold valuesTaste characteristics at 40 ppm: terpy, citrus, limelike, oily, green with a tropical fruity nuance.
General Descriptionγ-Terpinene, volatile essential oil derived from Melaleuca alternifolia, shows antimicrobial properties against various human pathogens. It is also extracted from Lippia multiflora. The antioxidant, anti-inflammatory and anti-proliferative activities of γ-terpinene is studied.
Flammability and ExplosibilityFlammable
PharmacologyCombinations of terpenes, such as terpinene, with nonionic surfactants and stabilizers have been patented for use as gallstone solvents. Artificial or human cholesterol calculi placed in terpinene with or without human bile at 37°C were dissolved within 1-2 hr (Hisamitsu Pharmaceutical Co., Inc., 1973).
Safety ProfileModerately toxic by ingestion. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
GAMMA-TERPINENE Preparation Products And Raw materials
Raw materialsAmmonia-->p-Cymene
Preparation ProductsCamphene-->2-Bornene-->Terpinolene-->ALPHA-PHELLANDRENE-->ALPHA-TERPINENE-->1,8-Cineole
mitiromycin TIMTEC-BB SBB006520 BTB 2,6-Ditert-butyl-p-benzoquinone-3-methyl-4-azine-2-benzothiazolinone SERATRODAST LABOTEST-BB LT00454561 GAMMA-TERPINENE altertoxin III GLYCINE THYMOL BLUE SODIUM SALT SALOR-INT L160326-1EA THYMOL BLUE-DIMETHYLFORMAMIDE SOLUTION THYMOL BLUE antimycin Mitomycin C LABOTEST-BB LT00455859 2,5-Di-tert-butyl-1,4-benzoquinone MC 77 THYMOLPHTHALEIN, MG SALT

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