WS-3-Spice database

2D:
3D:
CAS Number:	39711-79-0
ECHA EC Number:	254-599-0
FDA UNII:	6S7S02945H
CoE Number:	2298
Category:	flavoring agents
IUPAC Name:	WS-3
InChI :	InChI=1/C13H25NO/c1-5-14-13(15)12-8-10(4)6-7-11(12)9(2)3/h9-12H,5-8H2,1-4H3,(H,14,15)
Std.InChI:	InChI=1S/C13H25NO/c1-5-14-13(15)12-8-10(4)6-7-11(12)9(2)3/h9-12H,5-8H2,1-4H3,(H,14,15)
InChIKey :	VUNOFAIHSALQQH-UHFFFAOYAP
Std.InChIKey:	VUNOFAIHSALQQH-UHFFFAOYSA-N
SMILES :	CCNC(=O)C1CC(CCC1C(C)C)C
MDL:	MFCD00130071
Molar Refractivity :	63.67 ± 0.3 cm3 (est)
Parachor :	546.4 ± 6.0 cm3 (est)
Index of Refraction :	1.454 ± 0.02 (est)
Surface Tension :	29.1 ± 3.0 dyne/cm (est)
Density :	0.898 ± 0.06 g/cm3 (est)
Polarizability :	25.24 ± 0.5 10-24cm3 (est)

US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:

Google Scholar:	Search
Google Books:	Search
Google Scholar: with word "volatile"	Search
Google Scholar: with word "flavor"	Search
Google Scholar: with word "odor"	Search
Perfumer and Flavorist:	Search
Google Patents:	Search
US Patents:	Search
EU Patents:	Search
Pubchem Patents:	Search
PubMed:	Search
NCBI:	Search
JECFA Food Flavoring:	1601 N-ethyl 2-isopropyl-5-methylcyclohexanecarboxamide
DG SANTE Food Flavourings:	16.013 N-ethyl-2-isopropyl-5-methylcyclohexane carboxamide
FEMA Number:	3455 N-ethyl 2-isopropyl-5-methylcyclohexanecarboxamide
FDA:	No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF):	39711-79-0 ; N-ETHYL-2-ISOPROPYL-5-METHYLCYCLOHEXANE CARBOXAMIDE

Physical Properties:

Appearance:	white to pale yellow crystalline solid (est)
Assay:	98.00 to 100.00
Food Chemicals Codex Listed:	No
Melting Point:	91.00 to 93.00 °C. @ 760.00 mm Hg
Boiling Point:	340.55 °C. @ 760.00 mm Hg (est)
Vapor Pressure:	0.000085 mmHg @ 25.00 °C. (est)
Flash Point:	> 212.00 °F. TCC ( > 100.00 °C. )
logP (o/w):	3.717 (est)
Soluble in:
	alcohol
	water, 21.38 mg/L @ 25 °C (est)
Insoluble in:
	water

Organoleptic Properties:

mentholic minty alcoholic cooling alcoholic cooling mentholic cooling minty eucalyptus camphoreous cooling camphoreous minty

Cosmetic Information:

CosIng:	cosmetic data
Cosmetic Uses:	tonic

Suppliers:

Advanced Biotech

KOOLADA-3 SYNTHETIC

sds

99% min.

Odor: Weakly menthol

Anshul Specialty Molecules

N-Ethyl-P-Menthane Carboxamide (WS-3)

Apple Flavor & Fragrance

Beijing Lys Chemicals

Menthol carboxamide

Berjé

products/aromatic-chemicals/

Media

BeYonde

Cooling Agents-3 (WS-3)

BOC Sciences

For experimental / research use only.

N-Ethyl-2-(isopropyl)-5-methylcyclohexanecarboxamide

Glentham Life Sciences

N-Ethyl-p-menthane-3-carboxamide

K.L. Koh Enterprise

COOLER WS3/23

Kingchem Laboratories

WS-3

Odor: Cool, minty

Kun Shan P&A

WS-3 (Chinese Source)

O'Laughlin Industries

N-ETHYL-2-ISOPROPYL-5-METHYLCYCLOHEXANE CARBOXAMIDE

(> 99%)

Odor: MILD MINTY, NEARLY ODORLESS

Flavor: INTENSE LINGERING COOLING EFFECT

Santa Cruz Biotechnology

For experimental / research use only.

WS 3

Shanghai Vigen Fine Chemical

WS-3

Sigma-Aldrich

N-Ethyl-2-isopropyl-5-methylcyclohexanecarboxamide, 99%, FG

sds

Certified Food Grade Products

Flavor: Cooling, Fresh

Useful in mint, red fruit, other fruits

TCI AMERICA

For experimental / research use only.

N-Ethyl-p-menthane-3-carboxamide >98.0%(GC)

sds

Tianjin Danjun International

WS-3

Tocris Bioscience

For experimental / research use only.

WS 3

Vigon International

Menthol Carboxamide (WS-3)

Odor: Cooling,Minty,Medicinal

WholeChem

Menthol carboxamide

Safety Information:

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed. R 36 - Irritating to eyes. R 41 - Risk of serious damage to eyes. S 02 - Keep out of the reach of children. S 20/21 - When using do not eat, drink or smoke. S 24/25 - Avoid contact with skin and eyes. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 37/39 - Wear suitable gloves and eye/face protection.

Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in Use Information:

Category:
flavoring agents
Recommendation for WS-3 usage levels up to:
	not for fragrance use.

Maximised Survey-derived Daily Intakes (MSDI-EU):		0.40 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA):		127.00 (μg/capita/day)
Threshold of Concern:		90 (μg/person/day)
Structure Class:		III
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 9. Update in publication number(s): 18, 25
Click here to view publication 9
		average usual ppm	average maximum ppm
baked goods:		-	-
beverages(nonalcoholic):		10.00000	10.00000
beverages(alcoholic):		10.00000	10.00000
breakfast cereal:		-	-
cheese:		-	-
chewing gum:		1400.00000	2000.00000
condiments / relishes:		-	-
confectionery froastings:		10.00000	10.00000
egg products:		-	-
fats / oils:		-	-
fish products:		-	-
frozen dairy:		10.00000	10.00000
fruit ices:		10.00000	10.00000
gelatins / puddings:		-	-
granulated sugar:		-	-
gravies:		-	-
hard candy:		100.00000	150.00000
imitation dairy:		-	-
instant coffee / tea:		-	-
jams / jellies:		10.00000	10.00000
meat products:		-	-
milk products:		-	-
nut products:		-	-
other grains:		-	-
poultry:		-	-
processed fruits:		-	-
processed vegetables:		-	-
reconstituted vegetables:		-	-
seasonings / flavors:		-	-
snack foods:		66.00000	100.00000
soft candy:		-	-
soups:		-	-
sugar substitutes:		-	-
sweet sauces:		-	-

Safety References:

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 86, (FGE.86)[1] - Consideration of aliphatic and aromatic amines and amides evaluated by JECFA (65th meeting) - Scientific Opinion of the Panel on Food Additives - Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 86, Revision 1 (FGE.86Rev1): Consideration of aliphatic and aromatic amines and amides evaluated by JECFA (65th meeting)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 86, Revision 2 (FGE.86Rev2): Consideration of aliphatic and arylalkyl amines and amides evaluated by JECFA (65th meeting)
View page or View pdf

EPI System: View

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA Substance Registry Services (TSCA):39711-79-0

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :62907

National Institute of Allergy and Infectious Diseases:Data

WGK Germany:2

N-ethyl-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide

Chemidplus:0039711790

References:

Leffingwell:	Chirality or Article
	N-ethyl-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	39711-79-0
Pubchem (cid):	62907
Pubchem (sid):	135020214

Other Information:

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
tgsc:	Atomic Weights use for this web site
(IUPAC):	Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):	View
CHEMBL:	View
HMDB (The Human Metabolome Database):	HMDB37834
FooDB:	FDB016984
Export Tariff Code:	2924.29.9500
ChemSpider:	View

Potential Blenders and core components :

For Odor

No odor group found for these

camel grass oil
FR

cyclopentanone
FL/FR

laevo-mono

menthyl glutarate
FL/FR

laevo-

menthyl methyl ether
FL/FR

pinocarvone
FL/FR

aldehydic

iso

butyraldehyde
FL/FR

anisic

estragole
FL/FR

balsamic

iso

bornyl formate
FL/FR

camphoreous

dextro-

camphor
FL/FR

camphor tree bark oil
FL/FR

laevo-

fenchone
FL/FR

thujyl alcohol
FL/FR

citrus

ocimene quintoxide
FL/FR

earthy

3-

octanol
FL/FR

floral

cyclohexyl ethyl acetate
FL/FR

cyclohexyl propanol
FR

dihydrocarvyl acetate
FL/FR

2',4'-

dimethyl acetophenone
FL/FR

geranium oil china
FL/FR

ylang ylang flower oil
FL/FR

fruity

3-

benzyl-4-heptanone
FL/FR

2-

cyclopentyl cyclopentanone
FL/FR

lilac lactone
FL/FR

green

geranium absolute
FL/FR

thiogeraniol
FL/FR

herbal

artemisyl ketone
FL/FR

barosma betulina leaf oil
FL/FR

1,4-

cineole
FL/FR

costmary oil (chrysanthemum balsamita)
FR

2-

cyclohexyl cyclohexanone
FR

dehydroxylinalool oxide
FL/FR

iso

dihydrolavandulol
FR

(Z)-iso

dihydrolavandulyl acetate
FR

dill seed oil indian
FL/FR

6-

hydroxydihydrotheaspirane (mixture of isomers)
FL/FR

hyssop oil
FL/FR

para-

menthane-3,8-diol
FL/FR

myrtenol
FL/FR

3-

octyl acetate
FL/FR

laevo-

perillaldehyde
FL/FR

beta-

pinene
FL/FR

D-(+)-alpha-

pinene
FL/FR

piperitone
FL/FR

rosemary absolute
FL/FR

rosemary oil morocco
FL/FR

sabinene hydrate
FL/FR

common

tansy flower oil
FR

common

tansy flower oil dutch
FR

theaspirane
FL/FR

viridiflorol
FL/FR

licorice

sweet

basil oleoresin
FL/FR

mentholic

cornmint oil
FL/FR

cornmint oil china
FL/FR

cornmint oil india
FL/FR

cornmint oil terpeneless
FL/FR

laevo-

menthol
FL/FR

dextro,laevo-

menthol
FL/FR

dextro-neo

menthol
FL/FR

dextro,laevo-neo

menthol
FL/FR

(±)-

menthol
FL/FR

(±)-iso

menthone
FL/FR

(+)-

menthone
FL/FR

laevo-

menthyl acetate
FL/FR

menthyl acetate racemic
FL/FR

peppermint cyclohexanone
FL/FR

dextro-

piperitone
FL/FR

iso

pulegyl acetate
FL/FR

minty

agathosma crenulata leaf oil
FL/FR

laevo-

carveol
FL/FR

laevo-

carvone
FL/FR

cis-

carvone-5,6-oxide
FL/FR

carvyl acetate
FL/FR

carvyl propionate
FL/FR

cornmint oil japan
FL/FR

cyclohexanone
FR

dihydrocarveol
FL/FR

(+)-

dihydrocarvone
FL/FR

dextro-

dihydrocarvone
FL/FR

diosphenol
FL/FR

ethyl salicylate
FL/FR

bitter

fennel seed oil
FR

mentha longifolia oil
FR

dextro-2,8-para-

menthadien-1-ol
FL/FR

trans-para-2,8-1-

menthadienol
FL/FR

trans-para-

menthan-2-one
FL/FR

homo

menthol
FL/FR

(-)-

menthone
FL/FR

menthoxypropane diol
FL/FR

homo

menthyl acetate
FL/FR

2-

methyl cyclohexanone
FL/FR

methyl salicylate
FL/FR

pennyroyal oil
FL/FR

pennyroyal oil cuba
FL/FR

pennyroyal oil fractions
FL/FR

pennyroyal oil spain
FL/FR

pennyroyal oil uruguay
FL/FR

peppermint absolute
FL/FR

peppermint oil CO2 extract
FL/FR

peppermint oil idaho
FL/FR

peppermint oil mongolia
FL/FR

peppermint oil russia
FL/FR

peppermint oil terpeneless
FL/FR

beta-

phellandrene
FL/FR

piperitenone
FL/FR

laevo-

piperitone
FL/FR

iso

propyl tiglate
FL/FR

(-)-iso

pulegol
FL/FR

iso

pulegol
FL/FR

(R)-(+)-

pulegone
FR

iso

pulegone
FL/FR

iso

pulegyl formate
FL/FR

spearmint absolute
FL/FR

spearmint oil america
FL/FR

spearmint oil terpeneless
FL/FR

tetrahydrocarvone
FL/FR

vanillin menthoxypropane diol acetal
FL/FR

wintergreen oil
FL/FR

WS-23
FL/FR

pine

plectranthus glandulosus hook f. leaf oil cameroon
FR

spicy

trans-

carveol
FL/FR

laevo-

verbenone
FL/FR

sulfurous

buchu mercaptan
FL/FR

grapefruit menthane
FL/FR

thujonic

armoise oil
FR

common

tansy oil canada
FR

tonka

mint lactone
FL/FR

tropical

beta-

cyclocitral
FL/FR

woody

para-tert-

butyl cyclohexanone
FR

camphene
FL/FR

(+)-

camphene
FL/FR

cis-2-

pinanol
FR

For Flavor

No flavor group found for these

artemisyl ketone
FL/FR

(+)-

camphene
FL/FR

trans-

carveol
FL/FR

carvone
FL/FR

cyclopentanone
FL/FR

2-

cyclopentyl cyclopentanone
FL/FR

(+)-

dihydrocarvone
FL/FR

2',4'-

dimethyl acetophenone
FL/FR

(±)-N,N-

dimethyl menthyl succinamide
FL

lilac lactone
FL/FR

limonen-10-yl acetate
FL

dextro-2,8-para-

menthadien-1-ol
FL/FR

cis+trans-para-1(7)8-

menthadien-2-yl acetate
FL

trans-para-2,8-1-

menthadienol
FL/FR

para-

menthane-3,8-diol
FL/FR

dextro,laevo-neo

menthol
FL/FR

3-laevo-

menthoxy-2-methyl propane-1,2-diol
FL

menthyl acetate racemic
FL/FR

laevo-mono

menthyl glutarate
FL/FR

laevo-

menthyl methyl ether
FL/FR

menthyl propylene glycol carbonate
FL

2-

methyl cyclohexanone
FL/FR

beta-

phellandrene
FL/FR

(Z,Z)-

photocitral A
FL

D-(+)-alpha-

pinene
FL/FR

pinocarvone
FL/FR

piperitenone
FL/FR

piperitenone oxide
FL

iso

pulegone
FL/FR

iso

pulegyl formate
FL/FR

vanillin menthoxypropane diol acetal
FL/FR

laevo-

verbenone
FL/FR

viridiflorol
FL/FR

menthyl methyl lactate
FL

thujyl alcohol
FL/FR

aldehydic

iso

butyraldehyde
FL/FR

alliaceous

benzyl mercaptan
FL

aromatic

laevo-

perillaldehyde
FL/FR

camphoreous

camphene
FL/FR

camphor tree bark oil
FL/FR

laevo-

fenchone
FL/FR

6-

hydroxydihydrotheaspirane (mixture of isomers)
FL/FR

coffee

2-iso

propyl pyrazine
FL

cooling

1,4-

cineole
FL/FR

dextro,laevo-

menthol
FL/FR

laevo-

menthol
FL/FR

menthoxypropane diol
FL/FR

menthyl acetate
FL/FR

homo

menthyl acetate
FL/FR

sabinene hydrate
FL/FR

theaspirane
FL/FR

WS-5
FL

creamy

mint lactone
FL/FR

floral

dihydrocarvyl acetate
FL/FR

geranium oil china
FL/FR

ylang ylang flower oil
FL/FR

fruity

3-

benzyl-4-heptanone
FL/FR

green

cyclohexyl ethyl acetate
FL/FR

dihydrocarveol
FL/FR

dextro-

dihydrocarvone
FL/FR

geranium absolute
FL/FR

ocimene quintoxide
FL/FR

3-

octyl acetate
FL/FR

iso

propyl tiglate
FL/FR

thiogeraniol
FL/FR

herbal

2-

acetoxy-1,8-cineole
FL

barosma betulina leaf oil
FL/FR

hyssop oil
FL/FR

rosemary absolute
FL/FR

rosemary oil morocco
FL/FR

licorice

sweet

basil oleoresin
FL/FR

estragole
FL/FR

meaty

2-

methyl 3-(methyl thio) furan
FL

medicinal

dextro-

camphor
FL/FR

mentholic

cornmint oil
FL/FR

cornmint oil terpeneless
FL/FR

(±)-

menthol
FL/FR

dextro-neo

menthol
FL/FR

(+)-

menthone
FL/FR

peppermint cyclohexanone
FL/FR

minty

agathosma crenulata leaf oil
FL/FR

laevo-

carveol
FL/FR

laevo-<

Potential Uses:

FL	beverage
FL	mint
	oral care agents
FL	spice
FL	tonic

Occurrence (nature, food, other):

not found in nature

Synonyms:

	cyclohexanecarboxamide, N-ethyl-5-methyl-2-(1-methylethyl)-
N-	ethyl 2-isopropyl-5-methylcyclohexanecarboxamide
N-	ethyl 5-methyl-2-iso-propylcyclohexanecarboxamide
	ethyl menthane carboxamide
N-	ethyl-2-(isopropyl)-5-methylcyclohexanecarboxamide
N-	ethyl-2-isopropyl-5-methyl cyclohexane carboxamide
N-	ethyl-2-isopropyl-5-methylcyclohexane carboxamide
N-	ethyl-2-isopropyl-5-methylcyclohexanecarboxamide
N-	ethyl-4-menthane-3-carboxamide
N-	ethyl-5-methyl-2-(1-methyl ethyl) cyclohexane carboxamide
N-	ethyl-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide
N-	ethyl-5-methyl-2-(propan-2-yl)cyclohexanecarboxamide
N-	ethyl-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide
N-	ethyl-L-menthylformylamine
N-	ethyl-p-menthane-3-carboxamide
N-	ethyl-p-methane-3-carboxamide
N-	ethyl-para-menthane-3-carboxamide
N-	ethyl[5-methyl-2-(methylethyl)cyclohexyl]carboxamide
	ethylmenthanecarboxamide
	framidice 3
	koolada-3 synthetic (Advanced Biotech)
	menthol carboxamide
	methyl cyclohexane carboxamide
2-iso	propyl-5-methyl-cyclohexanecarboxylic acid ethylamide
	rightcool WS-3
	winsense extra 500
	WS-3
	WS3

Articles:

Info:aliphatic and aromatic amines and amides

PubMed:Release kinetics of actives from chewing gums into saliva monitored by direct analysis in real time mass spectrometry.