eugenol
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IUPAC Name - 2-methoxy-4-prop-2-enylphenol
InChI - InChI=1/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
InChIKey - RRAFCDWBNXTKKO-UHFFFAOYAJ
CAS Number : 97-53-0
(EINECS) Number :202-589-1
Beilstein Number :1366759
FEMA Number :2467
COE Number :171
Molar Refractivity :48.72 ± 0.3 cm3 (est)
Parachor :384.3 ± 4.0 cm3 (est)
Index of Refraction :1.535 ± 0.02 (est)
Surface Tension :36.5 ± 3.0 dyne/cm (est)
Density :1.050 ± 0.06 g/cm3 (est)
Polarizability :19.31 ± 0.5 10-24cm3 (est)
XlogP : 2.80 (est)
Molecular Weight : 164.2010800 (IUPAC) (PT) (112)
Formula :C10 H12 O2
Pherobase Floral:view
 
 
Category :cosmetic, flavor and fragrance agents

EU / EUROPA / FDA / JECFA Information :
JECFA Food Flavoring : 1529
Fl@vouring Number : 04.003
FDA Mainterm : EUGENOL.
FDA Regulation. :FDA PART 177 -- INDIRECT FOOD ADDITIVES: POLYMERS
Subpart C--Substances for Use Only as Components of Articles Intended for Repeated Use
Sec. 177.2800 Textiles and textile fibers.


FDA PART 184 -- DIRECT FOOD SUBSTANCES AFFIRMED AS GENERALLY RECOGNIZED AS SAFE
Subpart B--Listing of Specific Substances Affirmed as GRAS
Sec. 184.1257 Clove and its derivatives.

Suppliers :
Advanced Biotech :eugenol
98% min. natural
Berje :Eugenol
Citrus and Allied Essences :Eugenol Extra
USP FCC
Citrus and Allied Essences :Eugenol
99/100% FCC (natural)
Fleurchem :eugenol (ex bay)
natural
Fleurchem :eugenol (ex cinnamon leaf)
natural
Fleurchem :eugenol
Global Essence :EUGENOL
NATURAL
John D. Walsh :Eugenol
Mane :eugenol
(ex Clove bud)
Moellhausen :eugenol
99% min. natural kosher
Odor:  spicy, clove leaf
Flavor:  spicy
Nippon Terpene :Eugenol
98% up
Payand Betrand :Eugenol
Indonesia, Natural Isolated Constituent
Penta :eugenol extra
USP FCC
Polarome :EUGENOL
USP/FCC
Robertet :Eugénol
naturel
SAFC Global® :Eugenol
≥98%, FCC, Kosher, FG
Odor:  cinnamon; clove; spicy
SAFC Global® :Eugenol
≥98%, natural, Kosher
Odor:  cinnamon; clove; spicy
Symrise :Eugenol
Odor:  strong, warm-spicy, like clove
Flavor:  strong, like clove
Vigon :Eugenol
FCC
Odor:  STRONG AROMATIC ODOR OF CLOVE

Organoleptics :
Odor Type :spicy
Odor Strength :medium ,
recommend smelling in a 10.00 % solution or less
Odor Description:
at 10.00 % in dipropylene glycol.  
sweet spicy clove woody
Luebke, William tgsc, (1984)
Odor sample from :Givaudan Corporation
Odor Description:
at 1.00 %.  
Sweet, spicy, clove like, woody, with phenolic savory ham and bacon notes and cinnamon and allspice nuances
Mosciano, Gerard P&F 26, No. 3, 80, (2001)
Taste Description:
at 1.00 - 10.00 ppm.  
Sweet, warm spicy clove with phenolic and woody nuances
Mosciano, Gerard P&F 26, No. 3, 80, (2001)
Substantivity :52  Hour(s)

Properties :
Appearence :pale yellow to dark yellow clear liquid
Assay : 98.00 to 100.00 %   
Food Chemicals Codex Listed :Yes
Specific Gravity :1.06400 to 1.07000 @ 25.00 °C.
Pounds per Gallon - est. : 8.854 to 8.903
Specific Gravity :1.06100 to 1.06900 @ 20.00 °C.
Pounds per Gallon - est. : 8.839 to 8.906
Refractive Index :1.54400 to 1.58900 @ 20.00 °C.
Melting Point : -12.00 to -10.00 °C. @ 760.00 mm Hg
Boiling Point : 252.00 to 253.00 °C. @ 760.00 mm Hg
Boiling Point : 121.00 to 124.00 °C. @ 10.00 mm Hg
Acid Value : 1.00  max.  KOH/g
Vapor Pressure :0.10000 mm/Hg @ 20.00 °C.
Flash Point :> 200.00  °F.  TCC  ( > 93.33 °C. )
logP (o/w) : 2.27
Shelf Life : 24.00 month(s) or longer if stored properly.
Storage :store in cool, dry place in tightly sealed containers, protected from heat and light.

Safety :
Most important hazard(s) :Xn - Harmful.
  R 22 - Harmful if swallowed.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
R 42/43 - May cause sensitization by inhalation and skin contact.
S 02 - Keep out of the reach of children.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
Human Experience : 8 % solution: no irritation or sensitization.
Oral Toxicity(LD50) : 
  Oral-Rat    1930.00  mg/kg
PSEBAA  73,148,1950

Dermal Toxicity(LD50) : 
  Not determined
Inhalation Toxicity(LC50) : 
  Not determined
 

Safety in Use :
Category :cosmetic, flavor and fragrance agents
Maximised Survey-derived Daily Intakes (MSDI-EU) :950.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA) :3364.00 (μg/capita/day)
Threshold of Concern :1800 (μg/person/day)
Structure Class :I
 
IFRA Critical Effect :Sensitization
Fragrance usage is IFRA RESTRICTED. View Standard for complete information.
Please review all IFRA documents for complete information. (QRA)
IFRA categories : limits in the finished product: (For a description of the categories, refer to the IFRA QRA Information Booklet.)
Category 1 :
See Note (1)
0.20 % (1)Category 2 : 0.20 %
Category 3 : 0.50 %Category 4 : 0.50 %
Category 5 : 0.50 %Category 6 :
See Note (1)
4.30 % (1)
Category 7 : 0.40 %Category 8 : 0.50 %
Category 9 : 0.50 %Category 10 : 0.50 %
Category 11 :See Note (2)
 Notes :
 

For this material, for pragmatic reasons, restrictive levels allowed by the QRA for certain categories but actually being higher than those already in place before applying the QRA, will temporarily not be implemented until the end of a 5 year monitoring phase. At the end of the 5 years the position will be reevaluated again.

 

(1) IFRA would recommend that any material used to impart perfume or flavour in products intended for human ingestion should consist of ingredients that are in compliance with appropriate regulations for foods and food flavourings in the countries of planned distribution and, where these are lacking, with the recommendations laid down in the Code of Practice of IOFI (International Organisation of the Flavor Industry). Further information about IOFI can be found on its website (www.iofi.org).

 

(2) Category 11 includes all non-skin contact or incidental skin contact products. Due to the negligible skin contact from these types of products there is no justification for a restriction of the concentration of this fragrance ingredient in the finished product.

Recommendation for eugenol flavor usage levels up to :
  2000.0000 ppm in the flavor.

Safety References :
European Food Safety Athority(efsa) :Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...
msds :msds
EPI System :view
NLM Hazardous Substances Data Bank :search
IFRA :view standard
Chemical Carcinogenesis Research Information System :Search
Cancer Citations :Search
Toxicology Citations :Search
Carcinogenic Potency Database :Search
EPA GENetic TOXicology :Search
Env. Mutagen Info. Center :Search
NLM Developmental and Reproductive Toxicity :Search
National Toxicology Program :Search
Canada Domestic Sub. List :Yes
EPA Chem. Sub. Inventory : Yes
SCCNFP :opinion
 
WGK Germany :1
 
 
 
 
2-methoxy-4-prop-2-enylphenol
BioActivity Analysis :125977
dtp/nci :209525
(EINECS) Number :202-589-1
Chemidplus :000097530
EPA/NOAA CAMEO :hazardous materials
EPA Substance Registry Services :97-53-0
RTECS :SJ4375000 for cas# 97-53-0

References :
 
2-methoxy-4-prop-2-enylphenol
NIST Chemistry WebBook :4020944582
Pubchem :150398
Flavornet :97-53-0

Cosmetics :
Cosmetic Uses : denaturants
perfuming agents
tonic

Other :
CosIng :cosmetic data
 C of A
Dietary Supplements Labels Database : Search
FDA Everything Added to Food in the United States (EAFUS)View
Export Tariff Code :2909.50.4010
FMA :listed
Household Products : Search
RIFM :listed
VCF-Online: VCF Volatile Compounds in Food
Synonyms :
4-allyl catechol-2-methyl ether
4-allyl guaiacol
4-allyl-2-methoxyphenol
1-hydroxy-2-methoxy-4-propenyl benzene
4-hydroxy-3-methoxy-1-allyl benzene
2-methoxy-4-allyl phenol
2-methoxy-4-prop-2-enylphenol
2-methoxy-4,2-propen-1-yl phenol

Soluble in :
 fixed oils
 kerosene
 paraffin oil, slightly soluble in warm paraffin oil
 water, 2460 mg/L @ 25C (est)

Insoluble in :
 water

Potential Blenders :    note
 acetaldehyde ethyl phenethyl acetalFL/FR
 acetophenoneFL/FR
2-acetyl furanFL/FR
 allspice oilFL/FR
 allyl amyl glycolateFR
 allyl cyclohexyl propionateFL/FR
isoamyl benzoateFL/FR
alpha-amyl cinnamaldehydeFL/FR
isoamyl phenyl acetateFL/FR
isoamyl salicylateFL/FR
 amyris wood oilFL/FR
para-anisaldehydeFL/FR
para-anisyl acetateFL/FR
para-anisyl alcoholFL/FR
 atractylis absoluteFR
 bay leaf oilFL/FR
 beeswax absoluteFL/FR
 benzoin resinoid siamFL/FR
 benzyl acetateFL/FR
 benzyl isoeugenolFL/FR
 benzylidene acetoneFL
 bergamot oil bergaptene reduced italyFL/FR
 blood orange oil italyFL/FR
 bois de rose oil brazilFL/FR
isobutyl cinnamateFL/FR
isobutyl salicylateFL/FR
 caraway seed oilFL/FR
 cardamom seed oilFL/FR
 carnation absoluteFR
 cassia bark oil chinaFL/FR
 chocolate pyrazine AFL/FR
 cinnamyl alcoholFL/FR
 citronellolFL/FR
 clary sage oil franceFL/FR
 clove leaf oilFL/FR
 clover nitrileFR
 coconut absoluteFL/FR
 copaiba balsam oilFL/FR
 coriander seed oilFL/FR
 costmary oil (chrysanthemum balsamita)FR
 coumarinFR
 cubeb oilFL/FR
 currant bud absolute blackFL/FR
 cyclohexyl ethyl alcoholFL/FR
gamma-decalactoneFL/FR
 decanolFL/FR
 deertongue absoluteFR
 dihydroanetholFL/FR
 dihydrojasmoneFL/FR
 dimethyl benzyl carbinyl isobutyrateFR
 ethyl cinnamateFL/FR
 ethyl vanillinFL/FR
 eugenolFL/FR
isoeugenyl acetateFL/FR
 fennel seed oil sweetFL/FR
 floral pyranolFR
 frankincense oilFL/FR
 geraniolFL/FR
 geranium oil bourbonFL/FR
 ginger root oil chinaFL/FR
 guaiacwood oilFL/FR
 gurjun balsam oilFR
 heliotropinFL/FR
 heliotropyl acetoneFL/FR
 heliotropyl diethyl acetalFR
(Z)-3-hexen-1-yl benzoateFL/FR
(Z)-3-hexen-1-yl salicylateFL/FR
alpha-hexyl cinnamaldehydeFL/FR
 hyssop oilFL/FR
 immortelle absoluteFL/FR
 jasmin absolute concrete egyptFL/FR
 karo karounde absoluteFR
 labdanum resinoidFR
 lavandin oil abrialisFL/FR
 lavender absolute bulgariaFL/FR
 leerallFR
 lilyallFR
 linaloolFL/FR
laevo-linaloolFL/FR
 linalool oxideFL/FR
 linalyl acetateFL/FR
 maltolFL/FR
 methyl (E)-cinnamateFL/FR
 methyl cedryl ketoneFL/FR
alpha-methyl cinnamaldehydeFL/FR
 methyl isoeugenolFL/FR
2-methyl undecanal (aldehyde C-12 mna)FL/FR
beta-naphthyl ethyl etherFL/FR
 narcissus absoluteFR
 nerolFL/FR
gamma-nonalactone (aldehyde C-18)FL/FR
 nonanal (aldehyde C-9)FL/FR
 nonanolFL/FR
 nutmeg oilFL/FR
 ocean propanalFL/FR
 orange peel oil sweet c.p. brazilFL/FR
 orris pyridine 25% ipmFR
 palmarosa oilFL/FR
 patchouli ethanoneFR
 patchouli oilFL/FR
 peony alcoholFR
 pepper oil blackFL/FR
 petitgrain oilFL/FR
 phenethyl acetateFL/FR
 phenethyl alcoholFL/FR
 phenethyl salicylateFL/FR
3-phenyl propyl alcoholFL/FR
 raspberry ketoneFL/FR
 rhodinolFL/FR
 sandalwood oil east indianFL/FR
 santallFR
alpha-terpineolFL/FR
 tetrahydrolinaloolFL/FR
 tobacco dodecaneFR
 tonka bean absoluteFR
 treemoss absoluteFR
1-undecanolFL/FR
10-undecen-1-al (aldehyde C-11 undecylenic)FL/FR
 vanilla absolute 100%FL/FR
 vanillyl acetateFL/FR
 verymossFR
 violet methyl carbonateFR
 woody acetateFR
 woody propanolFR
 ylang ylang flower oilFL/FR

Potential Uses :
 acacia cassie farnesianaFR
 agate 
 almondFR
 amberFR
 angel 
 appleFR
 apricotFR
 aramis 
 azaleaFR
 balsamFR
 bananaFR
 bayFL/FR
 bay rumFR
 bayberryFR
 bellodgia 
 benzoin 
 blue grass 
 blue mist 
 bouquetFR
 camelia 
 carawayFL/FR
 carnation dianthus oeilletFR
 cassiaFR
 champaca champakFR
 cherryFR
 chocolate cacao 
 christmas blendsFR
 chypreFR
 cinnamonFR
 citronellaFL/FR
 citrusFR
 cloveFR
 dateFR
 eglantine sweet briarFR
 fern fougereFR
 fixer 
 floralFR
 florida breeze 
 forestFR
 forest pine forestFR
 gardeniaFR
 geraniumFR
 ginger whiteFR
 gingerbreadFR
 greenhouseFR
 heatherFR
 heliotropeFR
 herbalFR
 hollyberryFR
 honeysuckle chevrefeuilleFR
 hovenia 
 hyacinth jacintheFR
 incenseFR
 jasminFR
 leatherFR
 maceFR
 magnoliaFR
 majaFR
 meat smoked meat 
 millefleurs 
 mintFR
 muskFR
 myrrhFR
 narcissus narcisseFR
 neroliFR
 nut walnutFL
 orange blossomFR
 orchidFR
 orientalFR
 orris irisFR
 patchouliFR
 peachFR
 pearFR
 pimentoFL/FR
 plumFR
 poppy 
 powderFR
 pumpkin pieFR
 quinceFR
 rain springFR
 raspberryFR
 reseda mignonetteFR
 roseFR
 rose whiteFR
 sandalwoodFR
 sassafrasFR
 spiceFR
 stock evening scentedFR
 strawberryFR
 sweet peaFR
 tobacco flowerFR
 tuberoseFR
 vanillaFR
 violetFR
 wallflowerFR
 windsor soap 
 wisteria wistaria glycineFR
 witch hazelFR
 woodyFR
 ylang ylangFR

Natural Occurrence in :    note
 basil S
data pagebasil absolute sweet @ 26.49% S
data pagebasil oil CO2 sweet @ 12.40% S
data pagebasil oil sweet @ 4.00% S
data pagebasil oil sweet egypt @ 0.29% S
data pagebasil oil sweet poland @ 0.62% S
 bay  
data pagebay leaf oil @ 44.41-68.93% S
data pagebay leaf oil anise @ 1.0% S
data pagebay leaf oil clove @ 56.1% S
data pagebay leaf oil lemon @ 0.1% S
data pagebetel leaf oil @ 33.22% S
 cananga S
 carnation S
data pagecarnation absolute @ 3.60% S
 cascarilla S
 cassia  
data pagecassia bark oil china @ 3.63% S
data pagecassia leaf oil china @ 3.63% S
data pagechampaca absolute @ 0.20% S
data pagechampaca concrete @ 0.30% S
data pagecinnamon bark oil (cinnamomum zeylanicum blume) india @ 0.76% S
data pagecinnamon bark oil (cinnamomum zeylanicum blume) sri lauka @ 1.07-13.30% S
data pagecinnamon bark oil ceylon @ 3.63% S
data pagecinnamon fruit oil india @ 0.2-0.3% S
 cinnamon leaf oil S
data pagecinnamon leaf oil ceylon @ 93.94% S
data pagecinnamon oil CO2 extract @ 1.82-2.31% S
data pagecinnamon twig oil @ 4.03% S
data pagecistus oil @ 1.6% S
 citronella  
data pagecitronella oil china @ 2.29% S
data pagecitronella oil java @ 2.45% S
data pageclocimum oil india @ 77.60% S
 clove S
data pageclove bud oil @ 77.13% S
data pageclove leaf oil @ 80.97% S
data pageclove stem oil india @ 80.19% S
 coffee  
data pagecouroupita guianensis aubl. flower oil brazil @ 18.90% S
 currant black currant S
 davana S
data pagedill weed oil reunion @ 0.10% S
data pageestragon oil @ 2.1% S
data pagefeverfew flower oil @ 0.1% S
data pagefeverfew leaf oil belgium @ trace% S
data pageginger root oil CO2 extract @ 0.83% S
data pagehelichrysum arenarium (l.) moench oil hungary @ 0.40% S
data pagejasmin absolute china @ 7.28% S
data pagejasmin absolute concrete egypt @ 2.63% S
data pagejasmin absolute concrete india @ 2.00-3.95% S
data pagejasmin absolute concrete italy @ 1.86% S
data pagejasmin oil italy @ 1.79% S
data pagejasmin sambac absolute egypt @ 0.08% S
data pagelaurel bark oil @ 1.7% S
 laurel berry S
 laurel leaf S
data pagelaurel leaf oil @ 2.6% S
data pagelaurel leaf oil turkey @ 2.90% S
data pagelaurel stem oil @ 2.2% S
data pagelaurel wood oil @ 5.0% S
 lavender spike lavender S
 lemongrass  
 mace S
data pagemace oil CO2 extract @ trace% S
 marjoram  
 myrtle S
 nutmeg S
data pagenutmeg flower oil @ 0.71% S
data pagenutmeg leaf oil @ 0.10-2.16% S
data pagenutmeg oil hydrodistilled india @ 0.4% S
data pagenutmeg oil india @ 0.35% S
data pageocimum gratissimum l. oil brazil @ 19.26% S
 origanum  
data pageosmanthus absolute @ 1.90% S
 peach  
 peppermint S
data pagepimenta leaf oil @ 28.04% S
 pimento berry 87% S
data pagepimento berry oil @ 17.3% S
data pagepimento berry oil CO2 extract jamaica @ 14.9% S
data pageplectranthus glandulosus hook f. leaf oil cameroon @ 0.10% S
 raspberry  
 rose  
data pagerose absolute morocco @ 0.80% S
data pagerose oil otto bulgaria @ 0.82% S
 rosemary S
data pagesage oil england @ 0.10% S
data pagesage oil reunion @ trace% S
data pagesnake root oil canada @ 0.60% S
data pagestachys recta l. oil serbia @ 1.70% S
 strawberry S
data pagetagete oil egypt @ 0.17% S
 tagetes  
data pagetansy oil argentina @ 0.12% S
 tarragon  
data pagetejpat oil @ 78.00% S
 tolu balsam S
data pageturmeric oil china @ 0.21% S
data pageturmeric root oil hydrodistilled @ 1.08% S
data pagevalerian root oil @ trace-0.1% S
data pageviolet flower absolute @ % S
data pagewormwood oil cuba @ 0.07% S
data pageyarrow oil @ 0.40% S
 ylang ylang S
data pageylang ylang oil CO2 extract @ 0.03% S
data pageylang ylang oil I (cananga odorata hook. f. and thomas.) @ 0.20% S
data pageylang ylang oil II (cananga odorata hook. f. and thomas.) @ 0.29% S
data pageylang ylang oil III @ 0.06% S



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