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Substance Name: Eugenol [USP]
RN: 97-53-0
UNII: 3T8H1794QW
InChIKey: RRAFCDWBNXTKKO-UHFFFAOYSA-N

Note

  • A cinnamate derivative of the shikamate pathway found in CLOVE OIL and other PLANTS.

Molecular Formula

  • C10-H12-O2

Molecular Weight

  • 164.2028
 

Classification Codes

Classification Codes

  • Agricultural Chemical
  • Analgesic (Dental)
  • Anti-Infective Agents
  • Insect Attractant, Repellent and Chemosterilant
  • Mutation Data
  • Skin / Eye Irritant
  • Solvents
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3

Names and Synonyms

Name of Substance

  • 2-Methoxy-4-(2-propenyl)phenol
  • Allylguaiacol
  • Eugenol
  • Eugenol [USP]
  • Phenol, 2-methoxy-4-(2-propenyl)-

MeSH Heading

  • Eugenol

Synonyms

  • 1,3,4-Eugenol
  • 1-Hydroxy-2-methoxy-4-allylbenzene
  • 1-Hydroxy-2-methoxy-4-prop-2-enylbenzene
  • 1-Hydroxy-2-methoxy-4-propenylbenzene
  • 2-Methoxy-1-hydroxy-4-allylbenzene
  • 2-Methoxy-4-(2-propen-1-yl)phenol
  • 2-Methoxy-4-allylphenol
  • 2-Methoxy-4-prop-2-enylphenol
  • 2-Metoksy-4-allilofenol
  • 2-Metoksy-4-allilofenol [Polish]
  • 4-06-00-06337 (Beilstein Handbook Reference)
  • 4-Allyl-1-hydroxy-2-methoxybenzene
  • 4-Allyl-2-methoxyphenol
  • 4-Allylcatechol 2-methyl ether
  • 4-Allylcatechol-2-methyl ether
  • 4-Allylguaiacol
  • 4-Hydroxy-3-methoxy-1-allylbenzene
  • 4-Hydroxy-3-methoxyallylbenzene
  • 5-Allylguaiacol
  • AI3-00086
  • Allylguaiacol
  • BRN 1366759
  • Caryophyllic acid
  • Caswell No. 456BC
  • CCRIS 306
  • EC 202-589-1
  • EINECS 202-589-1
  • Engenol
  • EPA Pesticide Chemical Code 102701
  • Eugenic acid
  • Eugenol
  • Eugenol (natural)
  • FA 100
  • FEMA No. 2467
  • FEMA Number 2467
  • HSDB 210
  • NCI-C50453
  • NSC 209525
  • p-Allylguaiacol
  • p-Eugenol
  • Phenol, 2-methoxy-4-(2-propenyl)-
  • Phenol, 4-allyl-2-methoxy-
  • Synthetic eugenol
  • UNII-3T8H1794QW

Systematic Names

  • Eugenol
  • Phenol, 2-methoxy-4-(2-propen-1-yl)-
  • Phenol, 2-methoxy-4-(2-propenyl)-
  • Phenol, 4-allyl-2-methoxy-

Superlist Names

  • 2-Methoxy-4-(2-propenyl)phenol
  • Eugenol

Registry Numbers

CAS Registry Number

  • 97-53-0

FDA UNII

  • 3T8H1794QW

System Generated Number

  • 0000097530

Structure Descriptors

InChI

1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3

InChIKey

RRAFCDWBNXTKKO-UHFFFAOYSA-N

Smiles

COc1cc(ccc1O)CC=C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo oral 500mg/kg (500mg/kg) BEHAVIORAL: ATAXIA

GASTROINTESTINAL: NAUSEA OR VOMITING
Gastroenterology. Vol. 15, Pg. 481, 1950.
guinea pig LD50 oral 2130mg/kg (2130mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
hamster LD50 intratracheal 17mg/kg (17mg/kg) LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Archives of Toxicology. Vol. 59, Pg. 78, 1986.
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 250, Pg. 1148, 1960.
mouse LD50 intravenous 72mg/kg (72mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 164, Pg. 30, 1966.
mouse LD50 oral 3gm/kg (3000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
rat LC inhalation > 2580mg/m3/4H (2580mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Archives of Toxicology. Vol. 62, Pg. 381, 1988.
rat LD50 intratracheal 11mg/kg (11mg/kg) LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Archives of Toxicology. Vol. 59, Pg. 78, 1986.
rat LD50 oral 1930mg/kg (1930mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: COMA

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Proceedings of the Society for Experimental Biology and Medicine. Vol. 73, Pg. 148, 1950.
rat LDLo intraperitoneal 800mg/kg (800mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

KIDNEY, URETER, AND BLADDER: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Revue Medicale de la Suisse Romande. Vol. 16, Pg. 449, 1896.
rat LDLo subcutaneous 5gm/kg (5000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE WEAKNESS

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Revue Medicale de la Suisse Romande. Vol. 16, Pg. 449, 1896.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point -7.50E+00 deg C   EXP
Boiling Point 253.2 deg C   EXP
pKa Dissociation Constant 10.19 (none) 25 EXP
log P (octanol-water) 2.27 (none)   EXP
Water Solubility 2460 mg/L 25 EXP
Henry's Law Constant 4.81E-08 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 6.50E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.