(E)-1,2,4-Trimethoxy-5-prop-1-enylbenzol

MONOCLINIC NEEDLES FROM WATER

Needles from light petroleum

Yellow to medium brown, moderately viscous liquid with a pleasant, spicy aromatic odor. Acid value: max 4. Ester value: 3-20. Solubility 1 vol in 5 vol of 90% ethanol; solutions may be turbid /cis-asarone/

Practically insol in water; sol in alcohol, ether, glacial acetic acid, carbon tetrachloride, chloroform, petroleum ether

62-63 °C

Crystals. MP: 67 °C. Insoluble in water; soluble in alcohol /isomer not specified/

62 - 63 °C

INDEX OF REFRACTION: 1.5683 @ 20 °C/D; SADTLER REF NUMBER: 34263 (IR, PRISM)

Index of refraction: 1.5719 at 11 °C/D

Solid; [HSDB] Fine faintly yellow crystals; [MSDSonline]

Solid

Density: 0.940-0.980 at 25 °C/25 °C. Index of refraction: 1.5010-1.5160 at 20 °C/D. Specific optical rotation: -5 deg to +35 deg. /cis-asarone; European/

Density: 1.060-1.080 at 25 °C/25 °C. Index of refraction: 1.5500-1.55525 at 20 °C/D. Specific optical rotation: -2 deg to +6.5 deg. /cis-asarone; Indian/

Warning

H302 (91.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 130 reports by companies from 2 notifications to the ECHA C&L Inventory.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

The action of asarone and beta-asarone, alone or in combination with either reserpine or chloropromazine, on conditioned avoidance behavior in rats, fighting behavior in mice, and electroshock convulsions in rats was determined. ... Asarone potentiated the action of reserpine and chlorpromazine on conditioned avoidance behavior and fighting behavior; beta-asarone did not. ... Asarone potentiated the lethal effect of chlorpromazine during electroshock convulsions; beta-asarone did not. Pretreatment with Acorus oil, asarone, or beta-asarone did not increase the concentration of 5-hydroxytryptamine in rat brain. /Asarones/

/LABORATORY ANIMALS: Acute Exposure/ beta-Asarone doubled sleeping time with sodium pentobarbital in mice at a dose of 50 mg/kg bw i.p. and doubled the sleeping time with ethanol at a dose of 75 mg/kg. /beta-Asarone/

/LABORATORY ANIMALS: Acute Exposure/ ... a study was conducted of the biological properties of alpha-asarone (1-propenyl-2,4,5- methoxybenzol)--etherophenol, isolated by the authors from the roots of Asarum europaeum. It was determined that the LD50 of asarone for mice in enteral administration was 417.6 mg/kg, in intra-abdominal 310 mg/kg ...

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ... The drug alpha-asarone (3, 6 and 9 mg/kg bw, ip, for 30 days) ... was administered intraperitoneally 1/2 hr before the animals were exposed to noise-stress (100 dB for 4 hr/day, for 30 days) . ... All the three doses of alpha-asarone had an effectively protective role, by normalizing the increased superoxide dismutase and lipid peroxidation, decreased catalase, glutathione peroxidase, levels of reduced glutathione, Vitamins C and E and protein thiols due to noise exposure. Thus, action of alpha-asarone against noise-stress may be due its antioxidant property ...

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Groups of 25 male and 25 female rats were fed diets containing 0, 400, 800, or 2000 ppm (0, 0.04, 0.08, or 0.2%) beta-asarone for two years. A positive control group of the same size received 2500 ppm (0.25%) Jammu oil of calamus (JOC; /approx. 75% beta-asarone/). None of the group receiving 2000 ppm (0.2%) beta-asarone or 2500 ppm (0.25%) JOC survived more than 84 weeks; mortality was also increased on the 800 ppm (0.08%) dose. Median survival time in the females was less than in the males in these groups. The gross pathological changes observed were serous fluid in the abdominal and pleural cavities, liver and kidney changes, and tumourous masses in the intestinal tract. The tumors were identified as leiomyosarcomas of the small intestine and were found in one rat on 400 ppm (0.04%), six on 800 ppm (0.08%), nine on 2000 ppm (0.2%) and one on 2500 ppm (0.25%) JOC. All the test rats with leiomyosarcomas were males. The earliest tumor was observed in a rat 52 weeks old on the 2000 ppm (0.2%) dose. Two leiomyosarcomas were also noted in control females but the location differed from that of the tumors in the treated animals. Atrophy of cardiac muscle cells occurred in controls and all test groups but was most prominent in the 2000 ppm (0.2%) beta-asarone and 2500 ppm (0.25%) JOC groups. Cardiac fibrosis generally paralleled the incidence of cardiac atrophy. Fatty degeneration and fatty infiltration were also in the heart more severe in the treated groups. Thrombosis within the chambers of the heart was observed in the 800 and 2000 ppm (0.08 and 0.27%) beta-asarone and 2500 ppm (0.25%) JOC treated groups. Passive hyperemia of the lung, kidneys and liver was more prominent in the test than control animals indicating faulty cardiac function in the test animals. Incidence of hepatic angiectasis and hepatic coagulative necrosis also tended to increase with increasing beta-asarone dose. Both sexes on 800 and 2000 ppm (0.08 and 0.2%) beta-asarone and 2500 ppm (0.25%) JOC had slightly depressed body weights throughout the study; the males on 400 ppm (0.04%) ß-asarone also had depressed body weights at termination but the number of survivors was small. Hemoglobin, hematocrit, and red and white cell counts were normal except that when the test animals became sick they became anemic with lowered hemoglobin, hematocrit, and red cell count. /beta-Asarone/

For more Non-Human Toxicity Excerpts (Complete) data for TRANS-ASARONE (14 total), please visit the HSDB record page.

LD50 Rat oral 1010 mg/kg bw /beta-Asarone/

LD50 Mouse oral 184.2 mg/kg bw /beta-asarone/

LD50 Mouse oral 418 mg/kg

LD50 Mouse ip 310 mg/kg

Docking experiments using a number of published crystal structures of HMG-CoA reductase with the potent hypocholesterolemic agent alpha-asarone are described. The results indicate that alpha-asarone binds in the enzyme's active site. The methoxy groups play a key role in the binding and probably also in its biological activity, as shown by extensive SAR studies reported for analogues of alpha-asarone. The docking results will be valuable for the structure-based design of novel hypolipidemic agents.

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.

Fibrinolysin or agents that convert plasminogen to FIBRINOLYSIN.

Found in calamus oil from roots of Acorus calamus L.; Used as a grain fumigant and insect chemosterilant; Calamus oil is used in perfumes and alcoholic beverages, but use is limited by potential toxicity of beta-asarone; [HSDB] Asarones occur in nature as a mixture of two isomers alpha (trans) and beta (cis); [Merck Index]

Farming (Pesticides) [Category: Industry]

Grain fumigant, insect chemisterilant /isomer not specified/

Essential oil ... Calamus oil is used in perfumery for spicy-herbaceous notes: small quantities are also employed in the alcoholic beverage industry. However, use is legally restricted because of the potential toxicity of beta-asarone. /cis-asarone/

Tranquilizer ... chemisterilant for insects /asarone, i.e. 2,4,5-trimethoxy-1-propenylbenzene)/

cis-and trans-Asarone

494-40-6:; Benzene, 1,2,4-trimethoxy-5-(1-propen-1-yl)- (unspecified isomer); (E)-and (Z)-2,4,5-Trimethoxypropen-1-yl benzene); 2883-98-9:; α-Asarone; trans-Asarone; Benzene, 1,2,4-trimethoxy-5-(1-propenyl)-, (E)-; trans-Isoasarone; 5273-86-9:; ß-Asarone; cis-ß-Asarone; Benzene, 1,2,4-trimethoxy-5-(1-propenyl)-, (Z)-; cis-Isoasarone

IFRA_STD_110.pdf

40

IFRA 51st Amendment - Guidance for the use of IFRA Standards

Prohibition: This material should not be used as a fragrance ingredient_Restriction: This material should be used only in the limited quantity as stated in the Standard

SESHADRI, THIRUVENGADAM, PROC INDIAN ACAD SCI 32A, 110 (1950); SHARMA, DANDIYA, INDIAN J APPL CHEM 32, 236 (1969).

Either extracted from calamus oil or synthesized (Wittig reaction).

Calamus oil is obtained by steam distillation of fresh or unpeeled, dried roots of Acorus calamus L. (Araceae) ... The plant occurs in polyploid varieties and the corresponding essential oils differ predominantly in their content of beta-asarone (cis-isoasarone, 5273-86-9) /cis-asarone/

UV irridiation of trans-isoasarone formed cis-isoasarone & asaronaldehyde. The isomerization rate decreased the concentration from 0.5 to 0.1% in methanol. Solvent affected the reaction, with the concentrations of cis-asarone & asaronaldehyde after 5 hr being: hexane 58.5 & 3.6, ethanol 55.4 & 2.5, methanol 40.0 & 2.7, acetone 50.9 & 7.3 & benzene 5.0 & nil. The tincture contains chlorogenic acid which retarded isomerization in vitro. No isomerization was found in irradiated tinctures (brown glass bottles) or tablets of the root.

Indian Acorus calamus from the Jammu area is tetraploid and yields an oil containing approximately 75% beta-asarone; Acorus calamus from Kashmir is hexaploid and yields an oil containing approximately 5% beta-asarone (Vashist & Handa, 1964). /cis-asarone/