EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

WS-12
(1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide

Supplier Sponsors

CAS Number: 68489-09-8Picture of molecule3D/inchi
Nikkaji Web:J2.926.766I
MDL:MFCD11100191
XlogP3-AA:4.60 (est)
Molecular Weight:289.41859000
Formula:C18 H27 N O2
NMR Predictor:Predict (works with chrome or firefox)
Category:flavor enhancers, flavoring agents
 
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:2079 (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide
FLAVIS Number:16.123 (Old)
DG SANTE Food Flavourings:16.123 (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide
FEMA Number:4681 (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF):68489-09-8 ; (1R,2S,5R)-N-(4-METHOXYPHENYL)-5-METHYL-2-(1-METHYLETHYL)CYCLOHEXANECARBOXAMIDE
 
Physical Properties:
Appearance:white crystals (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 177.70 °C. @ 760.00 mm Hg
Boiling Point: 447.00 to 448.00 °C. @ 760.00 mm Hg (est)
Flash Point: 436.00 °F. TCC ( 224.60 °C. ) (est)
logP (o/w): 5.017 (est)
Soluble in:
 alcohol
 water, 0.5185 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Type: minty
Odor Strength:medium
Odor Description:at 100.00 %. cool minty
Flavor Type: cooling
cooling
Taste Description: cooling
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
WS-12 98%
M&U International
WS-12
Parchem
(1R,2S,5R)-N-(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexane-carboxamide
Renessenz (Symris)
Winsense™ WS-12 99.8% min
Santa Cruz Biotechnology
For experimental / research use only.
WS-12
Sigma-Aldrich: Sigma
For experimental / research use only.
WS-12 ≥98% (HPLC), powder
Tianjin Danjun International
WS-12
Tocris Bioscience
For experimental / research use only.
WS 12 >99 %
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the Chemical Sources Association
 
Safety Information:
Preferred SDS: View
 
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:
oral-rat LD50 [sex: F] > 2000 mg/kg
(Bradshaw, 2008)

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: flavor enhancers, flavoring agents
Recommendation for WS-12 usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 12.00 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 150 (μg/person/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: 25
 average usual ppmaverage maximum ppm
baked goods: 1.000005.00000
beverages(nonalcoholic): 1.000005.00000
beverages(alcoholic): 1.0000010.00000
breakfast cereal: 1.000005.00000
cheese: --
chewing gum: 100.00000500.00000
condiments / relishes: --
confectionery froastings: 1.0000010.00000
egg products: 1.0000010.00000
fats / oils: 1.0000010.00000
fish products: --
frozen dairy: 5.0000020.00000
fruit ices: 2.0000020.00000
gelatins / puddings: 2.0000020.00000
granulated sugar: 2.0000020.00000
gravies: --
hard candy: 2.0000020.00000
imitation dairy: 1.000005.00000
instant coffee / tea: 1.000005.00000
jams / jellies: 2.0000020.00000
meat products: --
milk products: 1.000005.00000
nut products: --
other grains: --
poultry: --
processed fruits: 1.000005.00000
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: 1.0000020.00000
soups: 1.0000020.00000
sugar substitutes: 1.0000020.00000
sweet sauces: --
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 0.500005.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 0.5000010.00000
Edible ices, including sherbet and sorbet (03.0): 0.5000010.00000
Processed fruit (04.1): 0.500005.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 1.0000020.00000
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 0.500005.00000
Bakery wares (07.0): 0.500005.00000
Meat and meat products, including poultry and game (08.0): --
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): --
Eggs and egg products (10.0): 0.5000010.00000
Sweeteners, including honey (11.0): 1.0000020.00000
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 1.0000020.00000
Foodstuffs intended for particular nutritional uses (13.0): --
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 0.100001.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 0.200001.00000
Ready-to-eat savouries (15.0): --
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): --
 
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):

Scientific Opinion on Flavouring Group Evaluation 304 (FGE.304): Five carboxamides from chemical group 30
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 304, Revision 1 (FGE.304Rev1): Four carboxamides from Chemical Groups 30
View page or View pdf

EPI System: View
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11266244
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide
 
References:
Leffingwell:Chirality or Article
 (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):11266244
Pubchem (sid):74660095
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (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):Search
FDA Listing of Food Additive Status:View
ChemSpider:View
 
Potential Blenders and core components note
For Odor
balsamic
iso
bornyl formate
FL/FR
dextro-
fenchone
FL/FR
camphoreous
beta-homo
cyclocitral
FL/FR
fenchol
FL/FR
laevo-
fenchone
FL/FR
citrus
ocimene quintoxide
FL/FR
earthy
(-)-alpha-
fenchol
FL/FR
ethereal
cyclohexyl formate
FL/FR
floral
iso
butyl salicylate
FL/FR
dihydrocarvyl acetate
FL/FR
fruity
cyclohexyl acetate
FL/FR
pineapple pentenoate
FL/FR
tropical trithiane
FL/FR
vanilla carboxylate
FL/FR
green
manzanate (Givaudan)
FL/FR
3,5,5-
trimethyl hexanol
FL/FR
herbal
1,4-
cineole
FL/FR
1,8-
cineole
FL/FR
geranic oxide
FL/FR
6-
hydroxydihydrotheaspirane (mixture of isomers)
FL/FR
hyssop oil
FL/FR
jambu oleoresin
FL/FR
spike
lavender oil
FL/FR
myrtenol
FL/FR
sabinene hydrate
FL/FR
theaspirane
FL/FR
medicinal
meta-
dimethyl hydroquinone
FL/FR
mentholic
cornmint oil china
FL/FR
cornmint oil terpeneless
FL/FR
dextro,laevo-
menthol
FL/FR
laevo-
menthol
FL/FR
(±)-
menthol
FL/FR
dextro-neo
menthol
FL/FR
(±)-iso
menthone
FL/FR
laevo-
menthyl acetate
FL/FR
menthyl acetate
FL/FR
peppermint cyclohexanone
FL/FR
minty
betula lenta bark oil america
FL/FR
cornmint oil japan
FL/FR
(-)-
menthone
FL/FR
(±)-
menthone
FL/FR
homo
menthyl acetate
FL/FR
laevo-
menthyl lactate
FL/FR
pennyroyal oil fractions
FL/FR
peppermint absolute
FL/FR
peppermint oil america
FL/FR
peppermint oil idaho
FL/FR
iso
pulegol
FL/FR
spearmint oil america
FL/FR
WS-23
FL/FR
naphthyl
para-
methyl anisole
FL/FR
odorless
dextro,laevo-
menthone glycerine acetal
FL/FR
spicy
4-
carvomenthenol
FL/FR
myrtenal
FL/FR
sulfurous
mango thiol
FL/FR
woody
camphene
FL/FR
(+)-
camphene
FL/FR
For Flavor
No flavor group found for these
(+)-
camphene
FL/FR
camphoreous
camphoreous
camphene
FL/FR
(-)-alpha-
fenchol
FL/FR
fenchol
FL/FR
laevo-
fenchone
FL/FR
geranic oxide
FL/FR
6-
hydroxydihydrotheaspirane (mixture of isomers)
FL/FR
chemical
meta-
dimethyl hydroquinone
FL/FR
cooling
(2S,5R)-N-[4-(2-
amino-2-oxoethyl)phenyl]-5-methyl-2-(propan-2-yl)cyclohexanecarboxamide
FL
iso
butyl salicylate
FL/FR
4-
carvomenthenol
FL/FR
1,4-
cineole
FL/FR
beta-homo
cyclocitral
FL/FR
1,3-
dihydroxyacetone (dimer)
FL
dextro-
fenchone
FL/FR
1-(2-
hydroxy-4-methyl cyclohexyl) ethanone
FL
jambu oleoresin
FL/FR
spike
lavender oil
FL/FR
manzanate (Givaudan)
FL/FR
dextro,laevo-
menthol
FL/FR
laevo-
menthol
FL/FR
iso
menthol
FL
laevo-
menthone 1,2-glycerol ketal
FL
dextro,laevo-
menthone glycerine acetal
FL/FR
menthyl acetate
FL/FR
homo
menthyl acetate
FL/FR
laevo-
menthyl lactate
FL/FR
mono
menthyl succinate
FL
2-(4-
methylphenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)acetamide
FL
peppermint oil america
FL/FR
N-(2-(
pyridin-2-yl)ethyl)-3-para-menthane carboxamide
FL
sabinene hydrate
FL/FR
theaspirane
FL/FR
WS-3
FL
WS-5
FL
earthy
panax quinquefolius root extract
FL
floral
dihydrocarvyl acetate
FL/FR
fruity
pineapple pentenoate
FL/FR
tropical trithiane
FL/FR
vanilla carboxylate
FL/FR
green
cyclohexyl formate
FL/FR
ocimene quintoxide
FL/FR
iso
phorone
FL
3,5,5-
trimethyl hexanol
FL/FR
herbal
hyssop oil
FL/FR
mentholic
cornmint oil terpeneless
FL/FR
dextro-neo
menthol
FL/FR
(±)-
menthol
FL/FR
peppermint cyclohexanone
FL/FR
minty
betula lenta bark oil america
FL/FR
1,8-
cineole
FL/FR
cornmint oil china
FL/FR
cornmint oil japan
FL/FR
limonene glycol
FL
(-)-
menthone
FL/FR
(±)-
menthone
FL/FR
(±)-iso
menthone
FL/FR
laevo-
menthyl acetate
FL/FR
myrtenal
FL/FR
myrtenol
FL/FR
pennyroyal oil fractions
FL/FR
peppermint absolute
FL/FR
peppermint oil idaho
FL/FR
iso
pulegol
FL/FR
spearmint oil america
FL/FR
WS-23
FL/FR
naphthyl
para-
methyl anisole
FL/FR
solvent
cyclohexyl acetate
FL/FR
sulfurous
mango thiol
FL/FR
woody
iso
bornyl formate
FL/FR
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 cyclohexanecarboxamide, N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-
(1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexane-carboxamide
(1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide
(1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide
(1R,2S,5R)-2-isopropyl-N-(4-methoxyphenyl)-5-methylcyclohexanecarboxamide
 

Articles:

PubMed:TRPM8 is the principal mediator of menthol-induced analgesia of acute and inflammatory pain.
Leffingwell & Associates:Flavor Properties of FEMA GRAS List 25 flavor chemicals
PubMed:Patient experiences at primary care practices using electronic health records.
PubMed:Practicability and sensitivity to change of the activities-specific balance confidence scale and 12-item Walking Scale for stroke.
PubMed:Blockade of TRPM8 activity reduces the invasion potential of oral squamous carcinoma cell lines.
PubMed:Sensitization of capsaicin and icilin responses in oxaliplatin treated adult rat DRG neurons.
PubMed:Characterization of selective TRPM8 ligands and their structure activity response (S.A.R) relationship.
PubMed:Menthol derivative WS-12 selectively activates transient receptor potential melastatin-8 (TRPM8) ion channels.
PubMed:Characterisation of TRPM8 as a pharmacophore receptor.
PubMed:Prospects for prostate cancer imaging and therapy using high-affinity TRPM8 activators.
 
Notes:
None found
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