Eugenol
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Eugenol
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CAS No:
97-53-0
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Formula:
C10H12O2
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Chemical Name:
Eugenol
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Synonyms:
Phenol,2-methoxy-4-(2-propen-1-yl)-;Phenol,4-allyl-2-methoxy-;Phenol,2-methoxy-4-(2-propenyl)-;2-Methoxy-4-(2-propen-1-yl)phenol;4-Allylguaiacol;4-Allyl-2-methoxyphenol;Caryophyllic acid;Eugenic acid;Eugenol;p-Allylguaiacol;p-Eugenol;2-Methoxy-4-allylphenol;4-Hydroxy-3-methoxyallylbenzene;2-Methoxy-1-hydroxy-4-allylbenzene;4-Allyl-1-hydroxy-2-methoxybenzene;1-Allyl-4-hydroxy-3-methoxybenzene;2-Hydroxy-5-allylanisole;3-(4-Hydroxy-3-methoxyphenyl)-1-propene;2-Methoxy-4-(2′-propenyl)phenol;3-(3-Methoxy-4-hydroxyphenyl)propene;2-Methoxy-4-(2-propenyl)phenol;Allylguaiacol;NSC 209525;NSC 8895;Dentogum;Bioxeda;2-Methoxy-4-[2-allyl]phenol;AQUI-S 20E;4-Allenylguaiacol
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CAS No:
Description
Eugenol is an essential oil found in cloves with antibacterial, anthelmintic and antioxidant activity. Eugenol is shown to inhibit lipid peroxidation.
Characteristics
29.5
2
Eugenol appears as clear colorless pale yellow or amber-colored liquid. Odor of cloves. Spicy pungent taste. (NTP, 1992)
1.0664 g/cm3 @ Temp: 20 °C
-9.2--9.1 °C
253.2 °C @ Press: 760 Torr
>212 deg F (>100 deg C) (closed cup)
1.536
H2O: slightly soluble ;Miscible with alcohol, chloroform, ether, oils; one mL dissolves in 2 mL 70% alcohol; soluble in glacial acetic acid, in aqueous fixed alkali hydroxide solutions
0-6ºC
<0.1 hPa (25 °C)
greater than 1.0 (NTP, 1992) (Relative to Air)
LD50 in rats, mice (mg/kg): 2680, 3000 orally (Hagan)
Combustible
Odor of cloves
Spicy, pungent taste
Safety Information
NONH for all modes of transport
1
R22;R38
S26-S36-S24/25
SJ4375000
Xn:Harmful;
Stable. Combustible. Incompatible with strong oxidizing agents.
P280-P305 + P351 + P338
H317-H319
Eugenol Use and Manufacturing
To a 500 ml 3 necked RBF equipped with an overhead stirrer, NGeneral procedure: MOM ether (5 mmol) and pTSA.H2O (7.7 mmol) weretriturated well in a mortar for 5 min (in the case of entry 10trituration time was about 15 min), reaction mixture was leftat room temperature for another 30 min. After completion ofthe reaction (monitored by TLC), cold water (4oC) wasadded. The products were separated by centrifugation. Theyields of the products ranged from 85-98percent. The purities andthe identities of the products were established by direct comparisonwith known compounds (TLC, Mp and IR). See supplementaryinformation for further details.General procedure: BiClNaAuCl4·2 H2O (39.8 mg, 0.1 mmol, 0.05 equiv) was added to a solution of silyl ether 1030 (557 mg, 2 mmol) in MeOH (4 mL) at r.t., and the mixture was stirred at r.t. for 7 h. The mixture was then diluted with EtOAc (10 mL), filtered through activated alumina, and concentrated in vacuo. The residue was purified by flash column chromatography[silica gel, EtOAc–PE (1:5)] to give a pale-yellow oil; yield: 286mg (87percent). 1H NMR (300 MHz, CDCl3): δ = 6.86–6.83 (m, 1 H), 6.69–6.67 (m, 2 H), 5.99–5.88 (m, 1 H), 5.49 (s, 1 H), 5.10–5.04 (m, 2 H), 3.87 (s, 3 H), 3.32(d, J = 6.6 Hz, 2 H).13C NMR (75 MHz, CDCl3): δ = 146.44, 143.92, 137.80, 131.89, 121.17, 115.45, 114.26, 111.14, 55.83, 39.84.MS (ESI, MeOH): m/z = 187 [M + Na]+.HRMS-ESI: m/z [M + Na]+ calcd for C10H12NaO2: 187.0735; found:187.0735.A mixture of nitroeugenol (0.72mmol), formaldehyde (0.72 mmol) and Zn powder (7.32mmol) was dissolved in 25 mL of ethanol. Formic acid (4.5mmol) was then added to the mixture. Reaction was heated at 65 °C for approximately 4.5 h and filtered while hot. Filtrate was extracted with dichloromethane (3 × 25 mL) and the organic phases were combined, which then dried with Na2SO4. Mixture was filtered and evaporated. Afterwards, the obtained product was analyzed by using GC-MS.To a 5ml_ Biotage® microwave vial fitted with a magnetic stirrer, was charged with calcium bis-triflimide (16 mg, 26.7 μιτιοΙ) and O-allylguaiacol (438 mg, 2.67 mmol). The vial was then sealed and the resultant homogeneous mixture was stirred for 2 minutes at the temperature of 200°C, under an autogenous pressure and a microwave irradiation generated by the Biotage® microwave instrument. After cooling to room temperature, the resulting reaction mixture was analysed by
eugenol is a botanical fraction. It is anti-bacterial, anti-inflammatory, and pain relieving. It can also be used as a local, topical anesthetic and antiseptic. In a cosmetic formulation, it can mask odor or provide fragrance. eugenol is a yellow, oily liquid and is generally associated with clove oil. However, it is also found in nutmeg, cinnamon, and bay leaf. Eugenol is a flavoring obtained from clove oil and also found in car- nation and cinnamon leaves. it is a stable, light yellow-green liquid of clove odor. it is slightly soluble in water and miscible in alcohol. it should be stored in glass or tin, avoiding iron containers. it is used in spice oils for application in condiments and meats at 100–200 ppm and in baked goods and candy at approximately 30 ppm. analgesic (topical), antiseptic, antifungal Eugenol is a dental compound which shows cytotoxicity to human oral squamous cell carcinoma and oral cells. When glucosylated, this compound exhibits anti-inflammatory activity. blood volume expander
Computed Properties
Molecular Weight:164.20
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:164.083729621
Monoisotopic Mass:164.083729621
Topological Polar Surface Area:29.5
Heavy Atom Count:12
Complexity:145
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Dispel wind and relieve pain, aromatic and clear the orifices, relieve itching and swelling
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