Asarone
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Asarone
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CAS No:
2883-98-9
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Formula:
C12H16O3
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Chemical Name:
Asarone
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Synonyms:
Benzene,1,2,4-trimethoxy-5-(1E)-1-propen-1-yl-;Benzene,1,2,4-trimethoxy-5-propenyl-,(E)-;Benzene,1,2,4-trimethoxy-5-(1-propenyl)-,(E)-;Isoasaron;Benzene,1,2,4-trimethoxy-5-(1E)-1-propenyl-;1,2,4-Trimethoxy-5-(1E)-1-propen-1-ylbenzene;Asaron;trans-Asarone;Asarum camphor;Asarone;α-Asarone;trans-Isoasaron;trans-Isoasarone;(E)-Asarone;α-Asaron;(E)-1,2,4-Trimethoxy-5-(prop-1-en-1-yl)benzene;1,2,4-Trimethoxy-5[(1E)-1-propenyl]benzene
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CAS No:
Description
Alpha-Asarone is one of the main psychoactive compounds, and possesses an antidepressant-like activity in mice.IC50 value:Target:In vitro: The results indicated that α-asarone significantly attenuated the LPS-stimulated increase in neuroinflammatory responses and suppressed pro-inflammatory cytokine production in BV-2 cells. Mechanistic study revealed that α-asarone?inhibited the LPS-stimulated activation via regulation of nuclear factor kappa-B by blocking degradation of inhibitor kappa
Solid
Alpha-asarone is the trans-isomer of asarone. It has a role as an anticonvulsant and a GABA modulator.
Asarone Basic Attributes
208.25
208.25
220-743-6
DQY9PNE5FK
107257
DTXSID20197784
MONOCLINIC NEEDLES FROM WATER|Needles from light petroleum
29093090
Characteristics
27.7
3
Solid
1.0±0.1 g/cm3
62-63 °C
296 °C @ Press: 760 Torr
107.7±23.8 °C
1.526
soluble in chloroform, methanol.
−20°C
1.5X10-3 mm Hg at 25 deg (est)
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/|Hnery's Law constant = 8.96X10-7 atm-cu cm/mol at 25 °C (est)|Hydroxyl radical reaction rate constant = 2.5X10-10 cu cm/molec-sec at 25 °C (est)
Safety Information
II; III
4.1
NONH for all modes of transport
3
22
22-24/25
DC2975000
Xn
P264, P270, P273, P301+P312, P330, P501
H302
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.
|Warning|H302 (92.19%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 128 companies from 2 notifications to the ECHA C&L Inventory.
Toxicity
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/
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
FROM ROOT OF ASARUM EUROPAEUM L, ARISTOLOCHIACEAE BY DISTILLATION WITH WATER. ALSO FOUND IN ETHEREAL OILS OF A EUROPAEUM & A ARIFOLIUM L, ARISTOLOCHIACEAE & IN ACORUS CALAMUS L, ARACEAE. ISOLATION: GATTERMANN, EGGERS, BER 32, 289 (1899).
Drug Information
/EXPTL THER/ The results of the present report show that alpha-asarone was an inhibitor of hepatic HMG-CoA reductase and that the administration of alpha-asarone at 80 mg/kg bw for 8 days decreased serum cholesterol by 38% (p < 0.001) in hypercholesterolemic rats. This alpha-asarone treatment affected mainly the serum LDL-cholesterol levels, leaving serum HDL-cholesterol lipoproteins unaffected, with a consequent decrease of 74% in the LDL/HDL ratio. In addition, alpha-asarone especially stimulated bile flow in hypercholesterolemic rats (60%), increasing the secretion of bile salts, phospholipids and bile cholesterol. The drug also reduced the cholesterol levels of gallbladder bile, whereas the concentration of phospholipids and bile salts increased only slightly, leading to a decrease in the cholesterol saturation index (CSI) of bile in the hypercholesterolemic rats. This CSI decrease and the increase in bile flow induced by alpha-asarone may account for the cholelitholytic effect of alpha-asarone. It seems that alpha-asarone induced clearance of cholesterol from the bloodstream and that the excess of hepatic cholesterol provided by LDL-cholesterol is diverted to bile sterol secretion via a bile choleresis process. The inhibition of HMG-CoA reductase and the increase in bile flow induced by alpha-asarone, as well as the decrease in the CSI, could then explain the hypocholesterolemic and cholelitholytic effects of alpha-asarone.|/EXPTL THER/ After daily dosing po of 80 mg/kg of alpha-asarone ... for seven days to hypercholesterolemic male rats, cholesterol decreased 57.3% ... and triglycerides diminished 42.5% ..., respectively. ... alpha-asarone decreased 80.6% the weight of gallstones in hamsters. ... Alpha-asarone did not produce any toxic effect after oral administration to rats of 10 or 50 mg/kg for 28 days, or genotoxicity by the dominant lethal test. ... No teratogenicity was observed in pregnant rats during organogenesis but in mice slight fetal toxicity was manifested by hydrocephaly, skeletal defects and fetal weight retardation ...|/EXPTL THER/ There was no significant difference between the antifungal activity of beta and alpha-asarone in crude drugs.
Fibrinolysin or agents that convert plasminogen to FIBRINOLYSIN. (See all compounds classified as Fibrinolytic 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. (See all compounds classified as Carcinogens.)
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.
/GENOTOXICITY/ The effect of alpha-asarone, a chemical with hypocholesterolemic properties on Sister Chromatid Exchange (SCE) induction was studied in human lymphocytes in vitro ... A slight but consistent increase in SCE was observed ...
(E)-asarone
Asarone Use and Manufacturing
Preparation of a-asarone via dehydrogenation of 2, 4, 5-trimethoxyphenylpropane with DDQ containing little amount of silica gel: Addition of a catalytic amount of silica gel (0.2-0. 6 g) drastically accelerated the rate of reaction as well as improved the yield of a-asarone when above dehydrogenation process (Example 11-a) was conducted under the same condition resulting a-asarone in 72% yield and trans-2, 4, 5- trimethoxycinnamaldehyde in 18% yield.Example II Preparation of a-asarone (trans-2, 4, 5-Trimethoxyphenylpropene) via dehydrogenation of 2, 4, 5-trimethoxyphenylpropane with DDQ: A solution of DDQ (2.04-2. 65 g) in anhydrous dioxane (40 mL) was added dropwise over a period of 10-15 min to a ice cold and well stirred solution of 2, 4, 5-trimethoxyphenylpropane (1.89g, 0.009 mol) in anhydrous dioxane (55 mL) and stirring was continued at room temperature for over night under inert atmosphere. The precipitated solid (DDQH2) was filtetred and further washed twice with dioxane. The combined dioxane was evaporated and concentrate was poured into water and then extracted with dichloromethane (3 x 70 mL). The combined organic layers were washed with brine (3 x 15 mL), 10% sodium bicarbonate (2 x 10 mL), brine (3 x 15 mL) and dried over anhydrous sodium sulphate. The residue obtained on evaporation of the solvents was chromatographed on silica gel column using hexane-ethyl acetate mixture with increasing proportion of ethyl acetate upto 40% and the fractions having similar Rf were mixed which after evaporation of the solvents provided two viscous liquids which were further crystallized from mixture of hexane and methanol to afford 0.90 g of a white solid (48%, mp 44-45 C) and 0.18 g of a yellow solid (9%, mp 139-140 C) as a side product. White solid (mp 44-45 C) as obtained above has Rf 0.63 (hexane: toluene: ethylacetate: : 1: 1: 0.1) ; IH NMR (CDC13) : 8 6.91 (1H, s, H-6), 6.64 (1H, dd, J=1. 5 Hz and 16 Hz, H-1'), 6.45 (1H, s, H-3), 6.02 (1H, dq, J=6.2 Hz and 16.0 Hz, H-2'), 3.84, 3.81 and 3.77 (each 3H, s, three OCH3), 1.87 (3H, dd, J=6.2 Hz and 1.5 Hz, H-3 3C NMR (CDC13) : 8 149.9 (C-2), 148.0 (C-4), 142.6 (C-5), 124.4 (C-1'), 123.4 (C-2'), 118. 3 (C-1), 109.2 (C-6), 97.3 (C-3), 56. 1, 55.7 & 55.1 (3-OCH3), 18.7 (C-3') ; EIMS m/z 208 (M+, 100), 193 (74), 177 (24), 165 (26), 137 (12), 105 (8), 91 (26), 77 (24), 69 (34), 65 (8), 53 (16). On the basis of above spectral data and comparing with reported literature (Patra, A. and Mitra, A. K. , J. Nat. Prod. 44, 668-669 (1981) and Gonzalez, M. C.; Sentandrew, M. A.; Rao, K. S.; Zafra, M. C. and Cortes, D. , Phytochemistry 43: 1361-1364 (1996) ), the white solid (mp 44-45 C) was identified as a-asarone. Yellow solid (mp 139-140 C) obtained as side product was identified as trans-2, 4, 5- trimethoxycinnamaldehyde having Rf= 0.45 (hexane-ethyl acetate; 4: 1);'H NMR 8 9.65 (IH, d, J=7.8 Hz, H-3'), 7.81 (1H, d, J=15. 8 Hz, H-1'), 7.03 (1H, s, H-6), 6.64 (1H, dd, J= 15.8 Hz, J=7.8 Hz, H-2'), 6.51 (1H, s, H-3), 3.95. 3.91 and 3.87 (each 3H, s, three OCH3) ; 3 C NMR 8 194.1 (C-3'), 154.1 (C-1'), 153.2 (C-2), 147.6 (C-4), 143.3 (C-5), 126.4 (C-2'), 114.5 (C-1), 110.5 (C-6), 96.5 (C-3), 56.4 (5-OCH3), 56.2 (2-OCH3), 56.0 (4-OCH3); EIMS m/z 222 [M] + (44), 207 (18), 191 (100), 179 (14), 171 (27), 151 (14), 147 (7), 69 (58), 58 (80); IR (film) vmax 1648 (conjugated carbonyl), 1602, 1504, 1466, 1448, 1350, 1254, 1120, 1024, 856 cm 1 ; UV (MeOH) kmax 244, 298, 366 nm. On the basis of above spectral data and comparing with reported literature, the yellow solid (mp 139- 140C) was identified trans-2, 4, 5-trimethoxycinnamaldehyde.
α-Asarone was used in the synthesis of series of α-asarone isomers and were investigated for their hypolipidemic and antiplatelet activities.
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/
PHENYLPROPANE DERIVATIVES WERE DETERMINED IN DRUGS & DRUG PREPARATIONS BY HPLC.
Computed Properties
Molecular Weight:208.25
XLogP3:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:208.109944368
Monoisotopic Mass:208.109944368
Topological Polar Surface Area:27.7
Heavy Atom Count:15
Complexity:203
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
It has the effects of relieving asthma, relieving cough, removing phlegm, sedation, antispasmodic, and anticonvulsant. Relieving asthma: It can counteract histamine and acetylcholine and relieve bronchospasm; relieving cough: It has a strong inhibitory effect on the cough center; removing phlegm: It causes increased secretion, thins thick sputum, reduces sputum viscosity, and makes it easier to cough up; sedation: It has a sedative effect close to diazepam, significantly reduces spontaneous activity without an inhibitory effect; antispasmodic: It is similar to aminophylline and has the effect of relaxing bronchial smooth muscles. Anticonvulsant: It can increase the electrical stimulation threshold of the cerebral cortex, inhibit the synaptic conduction of electrical stimulation and the spread of epileptic electricity, thereby preventing or alleviating epileptic seizures.
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