ISOEUGENOL

PRODUCT IDENTIFICATION

CAS NO. 97-54-1

ISOEUGENOL

EINECS NO. 202-590-7
FORMULA CH3OC6H3(CH=CHCH3)OH
MOL WT. 164.20

H.S. CODE

2909.50.4010

TOXICITY

Oral rat LD50: 1560 mg/kg
SYNONYMS 2-Methoxy-4-(1-propenyl) phenol; 4-Propenylguaiacol;

Isoeugenol; 1-(3-Methoxy-4-hydroxyphenyl)-1-propene; 1-Hydroxy-2-methoxy-4-propen-1-ylbenzene; 1-Hydroxy-2-methoxy-4-propenylbenzene; 2-Methoxy-4-(1-propenyl)phenol; 2-Methoxy-4-propenylphenol; 3-Methoxy-4-hydroxy-1-propen-1-ylbenzene; 4-Hydroxy-3-methoxy-1-propen-1-ylbenzene; 4-Hydroxy-3-methoxy-1-propenylbenzene; 4-Hydroxy-3-methoxypropenylbenzene;

SMILES c1(cc(ccc1O)\C=C/C)OC

CLASSIFICATION

 

EXTRA NOTES

FEMA No. 2468

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE clear to yellow liquid

MELTING POINT

-10 C
BOILING POINT 266 - 268 C
SPECIFIC GRAVITY 1.077

SOLUBILITY IN WATER

Slightly soluble

SOLVENT SOLUBILITY

soluble in alcohol, ether
pH  
VAPOR DENSITY 5.7

AUTOIGNITION

 

NFPA RATINGS

Health: 3; Flammability: 1; Reactivity: 0

REFRACTIVE INDEX

1.5760
FLASH POINT

112 C

STABILITY Stable under ordinary conditions

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking

Google Scholar Search

Drug Information Portal (U.S. National Library of Medicine) - Isoeugenol

PubChem Compound Summary - Isoeugenol

IPCS INCHEM -  Isoeugenol

KEGG (Kyoto Encyclopedia of Genes and Genomes) -  Isoeugenol

http://www.ebi.ac.uk/chebi/ -  Isoeugenol

http://www.ncbi.nlm.nih.gov/ -  Isoeugenol

Human Metabolome Database - Isoeugenol

Material Safety Data Sheet

http://www.pnas.org/
Phenylpropenes such as chavicol, t-anol, eugenol, and isoeugenol are produced by plants as defense compounds against animals and microorganisms and as floral attractants of pollinators. Moreover, humans have used phenylpropenes since antiquity for food preservation and flavoring and as medicinal agents. Previous research suggested that the phenylpropenes are synthesized in plants from substituted phenylpropenols, although the identity of the enzymes and the nature of the reaction mechanism involved in this transformation have remained obscure. We show here that glandular trichomes of sweet basil (Ocimum basilicum), which synthesize and accumulate phenylpropenes, possess an enzyme that can use coniferyl acetate and NADPH to form eugenol. Petunia (Petunia hybrida cv. Mitchell) flowers, which emit large amounts of isoeugenol, possess an enzyme homologous to the basil eugenol-forming enzyme that also uses coniferyl acetate and NADPH as substrates but catalyzes the formation of isoeugenol. The basil and petunia phenylpropene-forming enzymes belong to a structural family of NADPH-dependent reductases that also includes pinoresinol–lariciresinol reductase, isoflavone reductase, and phenylcoumaran benzylic ether reductase.

http://www.scribd.com/
Vanillin is undoubtedly one of the most popular and widely used flavoring agents in the world. Naturalvanillin is extracted from vanilla beans and is relatively expensive. Moreover, the consumer demand for natural vanillin highly exceeds the amount of vanillin extracted by plant sources. This had led to theinvestigation of alternative routes for its production such as microbial bioconversion. In this study, a novelstrain bacterium capable of converting isoeugenol to vanillin was isolated by conventional enrichment process from soils of spicy plants farms. On the basis of morphological and physiochemical characteristics,the isolate was identified asPseudomonassp. strain ISPC2. Vanillin formation was analyzed byspectrophotometery with thiobarbituric acid reagent and evaluated accurately by gas chromatography. Using10 g/l of isoeugenol as substrate in 25 ml reaction solution at 30 °C and 150 rpm, vanillin reached amaximum concentration of 1.15 g/l after 96 h reaction, corresponding to a molar yield of 12.4%. This strainshowed potential to be a good candidate for biotechnological production of vanillin from isoeugenol. Further studies for standardization and optimization for higher yield of vanillin production needs to be investigated

Local: Eugenol, allyl chain-substituted guaiacol (2-methoxyphenol), is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil and cinnamon. It is very slightly soluble in water and soluble in organic solvents. It has a spicy odor and taste of clove. Eugenol is used in perfumeries, flavorings, essential oils and in medicine (local antiseptic and analgesic). It is used in the production of isoeugenol for the manufacture of vanillin. Eugenol has wide application in dentistry for analgesic and antiseptic properties. Eugenol derivatives or methoxyphenol derivatives in wider classification are used in perfumery and flavoring. They are used in formulating insect attractants and UV absorbers, analgesics, biocides and antiseptics. They are also used in manufacturing stabilizers and antioxidants for plastics and rubbers. Isoeugenol is used in manufacturing perfumeries, flavorings, essential oils (odor description: Clove, spicy, sweet, woody) and in medicine (local antiseptic and analgesic) as well as vanillin.

SALES SPECIFICATION

APPEARANCE

clear to yellow liquid

ASSAY

99.0% min

SPECIFIC GRAVITY 1.078 - 1.085
REFRACTIVE INDEX 1.575 - 1.580
TRANSPORTATION
PACKING  
HAZARD CLASS  
UN NO.  
SAFETY INFORMATION

HAZARD OVERVIEW

OSHA Hazards:Harmful by ingestion., Skin sensitiser, Irritant. May cause respiratory tract irritation. May be harmful if swallowed. Causes eye and skin irritation.

GHS

 

SIGNAL WORD Warning

PICTOGRAMS

HAZARD STATEMENTS

H302 Harmful if swallowed.
H315 Causes skin irritation.
H317 May cause an allergic skin reaction.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.

PRECAUTIONARY  STATEMENTS

P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P280 Wear protective gloves.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

EC DIRECTIVES

 

HAZARD CODES

Xn Harmful

RISK PHRASES

22 Harmful if swallowed
36/37/38
Irritating to eyes, respiratory system and skin
43
May cause sensitization by skin contact

SAFETY PHRASES

26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37
Wear suitable protective clothing and gloves

PRICE INFORMATION