Eugenol

Modify Date: 2024-01-01 20:57:35

Eugenol Structure
Eugenol structure
 Common Name Eugenol
CAS Number 97-53-0 Molecular Weight 164.201
Density 1.1±0.1 g/cm3 Boiling Point 255.0±0.0 °C at 760 mmHg
Molecular Formula C10H12O2 Melting Point −12-−10 °C(lit.)
MSDS Chinese USA Flash Point 119.8±8.1 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Eugenol


Eugenol is an essential oil found in cloves with antibacterial, anthelmintic and antioxidant activity. Eugenol is shown to inhibit lipid peroxidation.

 Names

Name eugenol
Synonym More Synonyms

 Eugenol Biological Activity

Description Eugenol is an essential oil found in cloves with antibacterial, anthelmintic and antioxidant activity. Eugenol is shown to inhibit lipid peroxidation.
Related Catalog
Target

Bacterial, Parasite[1]

In Vitro The essential oil of O. gratissimum, as well as eugenol, are efficient in inhibiting eclodibility of H. contortus eggs, showing possible utilizations in the treatment of gastrointestinal helmintosis of small ruminants. At 0.50% concentration, the essential oil and eugenol show a maximum eclodibility inhibition[1]. Eugenol inhibits superoxide anion generation in xanthine-xanthine oxidase system to an extent of 50% at concentrations of 250 μM. Eugenol also inhibits the generation of hydroxyl radicals to an extent of 70%. The OH-radical formation measured by the hydroxylation of salicylate to 2, 3-dihydroxy benzoate is inhibited to an extent of 46% by eugenol at 250 μM[2]. Eugenol protects against RS-induced development of IBS-like gastrointestinal dysfunction through modulation of HPA-axis and brain monoaminergic pathways apart from its antioxidant effect. Eugenol (50 mg/kg) reduces 80% of RS-induced increase in fecal pellets similar to that of ondansetron. Eugenol attenuates 80% of stress-induced increase in plasma corticosterone and modulates the serotonergic system in the PFC and amygdala. Eugenol attenuates stress-induced changes in norepinephrine and potentiates the antioxidant defense system in all brain regions[3].
In Vivo Eugenol (33 mg/kg) administered orally for 2 days causes significant suppression of knee joint edema, which continues to be significantly reduced at the end of the treatment. After 2 days, eugenol-treated mycobacterial arthritic rats show a marked reduction in paw swelling[4].
Cell Assay The essential oil and eugenol are diluted in aqueous solution of Tween 20 (0.5%) in the following concentrations: 0.0625, 0.12, 0.25, 0.5 and 1.0% to be used in the egg hatch test[1].
Animal Admin Rats: The treatment groups of arthritic rats are given either ingwerol (0.33 mL/kg or 33 mg/kg) or eugenol (0.33 mL/kg or 33 mg/kg) orally 1 day prior to the induction of arthritis. This treatment is continued for 26 days on a daily basis. Mycobaterium trated rats receive physiological saline orally[4].
References

[1]. Pessoa LM, et al. Anthelmintic activity of essential oil of Ocimum gratissimum Linn. and eugenol against Haemonchus contortus. Vet Parasitol. 2002 Oct 16;109(1-2):59-63.

[2]. Reddy AC, et al. Studies on the inhibitory effects of curcumin and eugenol on the formation of reactive oxygenspecies and the oxidation of ferrous iron. Mol Cell Biochem. 1994 Aug 17;137(1):1-8.

[3]. Garabadu D, et al. Protective effect of eugenol against restraint stress-induced gastrointestinal dysfunction: Potential use in irritable bowel syndrome. Pharm Biol. 2015 Jul;53(7):968-74.

[4]. Sharma JN, et al. Suppressive effects of eugenol and ginger oil on arthritic rats. Pharmacology. 1994 Nov;49(5):314-8.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 255.0±0.0 °C at 760 mmHg
Melting Point −12-−10 °C(lit.)
Molecular Formula C10H12O2
Molecular Weight 164.201
Flash Point 119.8±8.1 °C
Exact Mass 164.083725
PSA 29.46000
LogP 2.20
Vapour Pressure 0.0±0.5 mmHg at 25°C
Index of Refraction 1.536
Stability Stable. Combustible. Incompatible with strong oxidizing agents.
Water Solubility slightly soluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
SJ4375000
CHEMICAL NAME :
Phenol, 4-allyl-2-methoxy-
CAS REGISTRY NUMBER :
97-53-0
BEILSTEIN REFERENCE NO. :
1366759
LAST UPDATED :
199701
DATA ITEMS CITED :
44
MOLECULAR FORMULA :
C10-H12-O2
MOLECULAR WEIGHT :
164.22
WISWESSER LINE NOTATION :
1U2R DQ CO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Human
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Human - man
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Mammal - pig
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - guinea pig
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1930 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - coma Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
LC - Lethal concentration
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2580 mg/m3/4H
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
800 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - muscle weakness Kidney, Ureter, Bladder - other changes
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
5 gm/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - muscle weakness Kidney, Ureter, Bladder - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intratracheal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
11 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - structural or functional change in trachea or bronchi Lungs, Thorax, or Respiration - acute pulmonary edema Lungs, Thorax, or Respiration - chronic pulmonary edema
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3 gm/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
72 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea Lungs, Thorax, or Respiration - respiratory stimulation
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
500 mg/kg
TOXIC EFFECTS :
Behavioral - ataxia Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
2130 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intratracheal
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
17 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - structural or functional change in trachea or bronchi Lungs, Thorax, or Respiration - acute pulmonary edema Lungs, Thorax, or Respiration - chronic pulmonary edema
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
68 gm/kg/34D-I
TOXIC EFFECTS :
Liver - other changes Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
70 gm/kg/14D-C
TOXIC EFFECTS :
Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
84 gm/kg/14D-C
TOXIC EFFECTS :
Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
37080 mg/kg/2Y-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Micronucleus test

MUTATION DATA

TYPE OF TEST :
Sister chromatid exchange
TEST SYSTEM :
Rodent - hamster Embryo
DOSE/DURATION :
300 ppb
REFERENCE :
SHIGAZ Shigaku. Ondotology. (Nippon Shika Daigaku Shigakkai, 1-9-20 Fujimi, Chiyodaku, Tokyo 102, Japan) V.38- 1949- Volume(issue)/page/year: 74,1365,1987 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 36,75,1985 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 TOXICOLOGY REVIEW FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 13,545,1975 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 82100 No. of Facilities: 1034 (estimated) No. of Industries: 17 No. of Occupations: 31 No. of Employees: 37569 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 82100 No. of Facilities: 9995 (estimated) No. of Industries: 82 No. of Occupations: 91 No. of Employees: 187937 (estimated) No. of Female Employees: 83766 (estimated)

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H317-H319
Precautionary Statements P280-P305 + P351 + P338
Personal Protective Equipment Faceshields;full-face respirator (US);Gloves;Goggles;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter
Hazard Codes Xn:Harmful;
Risk Phrases R22;R38
Safety Phrases S26-S36-S24/25
RIDADR NONH for all modes of transport
WGK Germany 1
RTECS SJ4375000
HS Code 29095090

 Synthetic Route

 Customs

HS Code 2909500000
Summary 2909500000 ether-phenols, ether-alcohol-phenols and their halogenated, sulphonated, nitrated or nitrosated derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

 Articles127

More Articles
Can Ocimum basilicum L. and Ocimum tenuiflorum L. in vitro culture be a potential source of secondary metabolites?

Food Chem. 194 , 55-60, (2015)

In this study Ocimum basilicum L. (OB) and Ocimum tenuiflorum L. (OT) in vitro culture standardisation for increasing eugenol distribution, in comparison to their respective field grown parts was carr...

Volatile Compounds from Grape Skin, Juice and Wine from Five Interspecific Hybrid Grape Cultivars Grown in Québec (Canada) for Wine Production.

Molecules 20 , 10980-1016, (2015)

Developed from crosses between Vitis vinifera and North American Vitis species, interspecific hybrid grape varieties are becoming economically significant in northern areas, where they are now extensi...

Effect of essential oils, such as raspberry ketone and its derivatives, on antiandrogenic activity based on in vitro reporter gene assay.

Bioorg. Med. Chem. Lett. 20 , 2111-4, (2010)

The effect of essential oils, such as raspberry ketone, on androgen (AR) receptor was investigated using a MDA-kb2 human breast cancer cell line for predicting potential AR activity. Among them, eugen...

 Synonyms

4-Allyl-2-methoxyphenol
Eugenic acid
p-Allylguaiacol
2-methoxy-4-allyl phenol
2-methoxy-4-(prop-2-en-1-yl)phenol
Eugenol
2U1R DQ CO1
4-allylguaiacol
2-methoxy-4-(2-propen-1-yl)phenol
p-Eugenol
femano.2467
EINECS 202-589-1
1-allyl-4-hydroxy-3-methoxybenzene
2-Methoxy-4-allylphenol
Engenol
FA 100
Caryophyllic acid
FEMA 2467
Phenol, 2-methoxy-4-(2-propen-1-yl)-
MFCD00008654
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