Dipentene appears as a colorless liquid with an odor of lemon. Flash point 113°F. Density about 7.2 lb /gal and insoluble in water. Hence floats on water. Vapors heavier than air. Used as a solvent for rosin, waxes, rubber; as a dispersing agent for oils, resins, paints, lacquers, varnishes, and in floor waxes and furniture polishes.
After oral administration, major metabolite in urine was perillic acid 8,9-diol in rats and rabbits, perillyl-beta-d-glucopyranosiduronic acid in hamsters, p-menth-1-ene-8,9-diol in dogs, and 8-hydroxy-p-menth-1-en-9-yl-beta-d-glucopyranosiduronic acid in guinea pigs and man.
来源:Hazardous Substances Data Bank (HSDB)
代谢
从兔尿中分离出的代谢物被鉴定为p-薄荷-1,8-二烯-10-醇。
... A metabolite isolated from rabbit urine was identified as p-mentha-1,8-dien-10-ol. ...
Limonene given orally to humans yields the following major plasma metabolites: perillic acid, limonene-1,2-diol, limonene-8,9-diol, and dihydroperillic acid, probably derived from perillic acid. Limonene (unchanged) and perillic acid artifacts (methyl ester) were also detected as minor plasma metabolites. Peak plasma levels for all metabolites were achieved 4-6 hours after administration, with the exception of limonene-8,9-diol which reached its peak level one hour after administration. Phase II glucuronic acid conjugates have been identified in the urine of human volunteers for all major and minor metabolites. They include the glucuronic acid conjugates of perillic acid, dihydroperillic acid, limonene-8,9-diol, limonene-10- ol, limonene-6-ol, and limonene-7-ol (perillyl alcohol).
IDENTIFICATION AND USE: Limonene is a colorless liquid. It is not registered for current pesticide use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. Limonene is used as a solvent in degreasing metals prior to industrial painting, for cleaning in the electronic and printing industries, and in paint as a solvent. Limonene is also used as a flavor and fragrance additive in food, household cleaning products and perfumes. It is also used as gallstone solubilizer. HUMAN EXPOSURE AND TOXICITY: Limonene is a skin irritant in humans. The oxidized forms of limonene are known to cause allergic contact dermatitis. Limonene liquid has been reported to irritate eyes, ingestion causes irritation of GI tract. Albuminuria and hematuria are probable if ingested in sufficient quantity. It is also associated with mouth and throat irritation, shortness of breath, and impaired lung function. ANIMAL STUDIES: Limonene is a skin irritant in experimental animals. The critical organ in animals (except for male rats) following oral or ip administration is the liver. Exposure to limonene affects the amount and activity of different liver enzymes, liver weight, cholesterol levels and bile flow. These changes have been noted in mice, rats and dogs. Limonene and its epoxides were not mutagenic when tested at concentrations of 0.3-3333 ug/plate in in vitro assays using different strains of Salmonella typhimurium, in the presence or absence of metabolic activation. When incubated with Syrian hamster embryo cells up to 100 ug/mL or 3 mM, limonene did not induce statistically significant cell transformation. There is no evidence that limonene was teratogenic or produced embryotoxic effects in the absence of maternal toxicity. ECOTOXICITY STUDIES: Terrestrial organisms are most likely exposed to limonene via the air. The few studies of terrestrial species (i.e. insects) using vapor exposure revealed effects of limonene at ppm levels. In the aquatic environment, limonene exhibits high acute toxicity to fish and Daphnia.
Evaluation: There is inadequate evidence in humans for the carcinogenicity of d-limonene. There is sufficient evidence in experimental animals for the carcinogenicity of d-limonene. Overall evaluation: In making its overall evaluation of the carcinogenicity to humans of d-limonene, the Working Group concluded that d-limonene produces renal tubular tumors in male rats by a non-DNA reactive alpha-2u-globulin associated response. Therefore, the mechanism by which d-limonene incr the incidence of renal tubular tumors in male rats is not relevant to humans. d-Limonene is not classifiable as to its carcinogenicity to humans (Group 3). /d-Limonene/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
副作用
神经毒素 - 急性溶剂综合征
Neurotoxin - Acute solvent syndrome
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
毒理性
毒性数据
LC50（小鼠）= 67,500 毫克/立方米
LC50 (mice) = 67,500 mg/m3
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
Inhalation of ozone (O3), a highly toxic environmental pollutant, produces airway inflammation and exacerbates asthma. However, in indoor air, O3 reacts with terpenes (cyclic alkenes), leading to formation of airway irritating pollutants. The aim of the study was to examine whether inhalation of the reaction products of O3 and the terpene, limonene, as well as limonene and low-level O3 by themselves, induced allergic sensitization (formation of specific immunoglobulin [Ig] E) and airway inflammation in a subchronic mouse inhalation model in combination with the model allergen ovalbumin (OVA). BALB/cJ mice were exposed exclusively by inhalation for 5 d/wk for 2 wk and thereafter once weekly for 12 wk. Exposures were low-dose OVA in combination with O3, limonene, or limonene/O3 reaction products. OVA alone and OVA + Al(OH)3 served as control groups. Subsequently, all groups were exposed to a high-dose OVA solution on three consecutive days. Serum and bronchoalveolar lavage fluid were collected 24 hr later. Limonene by itself did not promote neither OVA-specific IgE nor leukocyte inflammation. Low-level O3 promoted eosinophilic airway inflammation, but not OVA-specific IgE formation. The reaction products of limonene/O3 promoted allergic (OVA-specific IgE) sensitization, but lung inflammation, which is a characteristic of allergic asthma, was not observed. In conclusion, the study does not support an allergic inflammatory effect attributed to O3-initiated limonene reaction products in the indoor environment.
The data suggest that monoterpenes are poorly resorbed in the GI tract. The resorbed portion of hydrocarbons accumulates in the lipophilic body compartments and is metabolized and then excreted by the kidneys. /Monoterpenes/
Percutaneous absorption of radioactive limonene from foam bath was measured in animals. Maximum blood level reached after 10 min of exposure and the concentration was proportional to the skin exposed.
...SKH-1 mice received topical or oral administration of limonene in the form of orange oil every day for 4 weeks ... Plasma and mammary pads were collected 4 hr after the final dosing. The mouse disposition study showed that topical and oral orange oil administration resulted in similar mammary tissue disposition of limonene with no clinical signs of toxicity ... Our studies showed that limonene is bio available in mammary tissue after topical orange oil application in mice ...
The kinetics, stereochemistry, and deuterium isotope effects in the α-pinene pyrolysis. Evidence for incursion of multiple conformations of a diradical
α-pinene at 256.7°C for 2400 s gave dipentene with twice as much deuterium as hydrogen transfer with kH/kD=1.49 and alloocimine with a Z and E trideuteriomethyl ratio of ca. 5 with kH/kD=0.89. The isotope effect on loss of starting material was 1.16. Separation of the enantiomers of α-pinene from 3600 s pyrolyses at 256.7°C followed by NMR analysis revealed that the ratio of the R-syn to R-anti to S-anti
旋光性α-pine烯的热解得到95％的外消旋柠檬烯（二戊烯），别甲胺，外消旋的α-pine烯，α-py烯。报告激活参数。（S）syn -6-trideuteriomethylα-pinene在256.7°C的温度下热解2400 s，生成的二戊烯的氘量是氢转移的两倍，k H / k D = 1.49，Z和E的三异氘甲基比值约26。5 ķ ħ / ķ d = 0.89。同位素对原料损失的影响为1.16。在256.7°C下从3600 s热解中分离出α-pine烯的对映体，然后进行NMR分析，结果表明[R -顺式到- [R -抗到小号-反异构体是4.6：3.7：1，在大约两个半衰期。动力学分析表明，先前提出的涉及两个具有C s对称性的双自由基缓慢相互转化的转化机理与α-pine烯异构体的分布不一致，特别是与键相比更多的表面保留产物（R - anti）的形成-旋转异构体（S - anti）。另一个的
Substituted bicyclooctenemethanols
申请人：International Flavors & Fragrances Inc.
公开号：US04166916A1
公开（公告）日：1979-09-04
The use of unsaturated bicyclooctenemethanols to augment or enhance the organoleptic properties of perfumes, tobaccos and perfumed articles and particularly the aroma of perfumes and perfumed articles and the aroma and taste of tobaccos, together with compositions containing such bicyclooctenemethanols and processes for preparing them, said bicyclooctenemethanols having the generic structures: ##STR1## wherein the wavy line represents exo or endo configurations of the ethanol moiety with respect to the carbon-carbon double bond of the bicyclooctene moiety; and intermediates useful in processes for preparing such bicyclooctenemethanols which intermediates have the structures: ##STR2## wherein X is a halogen selected from the group consisting of chlorine, bromine and iodine.
Substituted bicyclooctenemethanols, process for producing same and uses
申请人：International Flavors & Fragrances Inc.
公开号：US04163737A1
公开（公告）日：1979-08-07
The use of unsaturated bicyclooctenemethanols to augment or enhance the organoleptic properties of perfumes, particularly the aroma of perfumes together with compositions containing such bicyclooctenemethanols and processes for preparing them, said bicyclooctenemethanols having the generic structures: ##STR1## wherein the wavy line represents exo or endo configurations of the ethanol moiety.
Sweetening with cycloalkyl ethers and thioethers of dipeptides
申请人：General Foods Corporation
公开号：US04676989A1
公开（公告）日：1987-06-30
The following dipeptides possess a high order of sweetness: ##STR1## wherein X=O or S; R is alkyl containing 1-3 carbon atoms; R.sub.1 is cycloalkyl, cycloalkenyl, lower alkyl-substituted cycloalkyl or cycloalkenyl, bicycloalkyl, bicycloalkenyl, tricycloalkyl, cyclic ether, cyclic thioether, cyclic sulfoxides, cyclic sulfones, aryl, benzyl, alkylaryl, aromatic heterocyclic or alkyl substituted aromatic heterocyclic containing up to 10 ring carbon atoms and up to a total of 12 carbon atoms; R.sub.2, R.sub.3, R.sub.4 and R.sub.6 are each H or lower alkyl; R.sub.5 is H, lower alkyl or cycloalkyl containing 3-5 ring carbons; each n=0, 1 or 2; m=0 or 1; Z is an alkylene chain containing 0-2 carbon atoms in the principal chain and up to a total of 6 carbon atoms; and food-acceptable salts.
Process for augmenting or enhancing the aroma of a detergent using
申请人：International Flavors & Fragrances Inc.
公开号：US04267067A1
公开（公告）日：1981-05-12
Described is a process for augmenting or enhancing the aroma of a solid or liquid anionic, cationic or nonionic detergent comprising the step of intimately admixing with a solid or liquid anionic, cationic or nonionic detergent base an aroma augmenting or enhancing quantity of 1,3,5,5-tetramethyl-2-oxabicyclo[2.2.2]octane.
