2-methyl cyclohexanone
2-methylcyclohexanone
 
Notes:
Used as a food additive [EAFUS]
  • BOC Sciences
    • BOC Sciences
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      Product(s):
      583-60-8 2-Methylcyclohexanone 98%
       
  • Penta International
    • Penta International Corporation
      Chemistry innovation
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      For over 30 years, Penta Manufacturing Company has played a growing role in worldwide chemistry innovations and applications. As an industry leader, Penta continues to pioneer chemistry-based solutions for practically every area of commerce. Our products and expertise have helped fuel technical advances in dozens of commercial applications including flavoring, coloring, fragrances and chemical processes.
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      Product(s):
      13-37300 2-METHYLCYCLOHEXANONE
       
  • Sigma-Aldrich
  • TCI AMERICA
    • TCI AMERICA
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      Product(s):
      M0197 2-Methylcyclohexanone >96.0%(GC)
       
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CAS Number: 583-60-8Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 209-513-6
FDA UNII: 56E8224ZFJ
Nikkaji Web: J3.301D
Beilstein Number: 0506751
MDL: MFCD00001635
XlogP3-AA: 1.50 (est)
Molecular Weight: 112.17184000
Formula: C7 H12 O
NMR Predictor: Predict (works with chrome or firefox)
EFSA/JECFA Comments: Racemate.
Category: flavor and fragrance 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: 1102  2-methylcyclohexanone
DG SANTE Food Flavourings: 07.179  2-methylcyclohexanone
FEMA Number: 3946 2-methylcyclohexanone
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF):583-60-8 ; 2-METHYLCYCLOHEXANONE
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Physical Properties:
Appearance: colorless clear liquid (est)
Assay: 96.00 to 100.00 % 
Food Chemicals Codex Listed: No
Specific Gravity: 0.92400 to 0.92600 @  25.00 °C.
Pounds per Gallon - (est).: 7.689 to  7.705
Refractive Index: 1.44400 to 1.45000 @  20.00 °C.
Boiling Point: 162.00 to  163.00 °C. @ 760.00 mm Hg
Vapor Pressure: 2.039000 mmHg @ 25.00 °C. (est)
Flash Point: 116.00 °F. TCC ( 46.67 °C. )
logP (o/w): 1.356 (est)
Soluble in:
 alcohol
 water, 5142 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
 
Odor Type: minty
 
 minty  peppermint  cooling  
Odor Description:
at 10.00 % in dipropylene glycol. 
minty peppermint cooling
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
Synonyms   Articles   Notes   Search   Top
Suppliers:
BOC Sciences
For experimental / research use only.
2-Methylcyclohexanone 98%
EMD Millipore
For experimental / research use only.
2-Methylcyclohexanone
Parchem
2-methyl cyclohexanone
Penta International
2-METHYLCYCLOHEXANONE
Santa Cruz Biotechnology
For experimental / research use only.
2-Methylcyclohexanone
Sigma-Aldrich
2-Methylcyclohexanone, ≥98%
Certified Food Grade Products
TCI AMERICA
For experimental / research use only.
2-Methylcyclohexanone >96.0%(GC)
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Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 10 - Flammable.
R 20 - Harmful by inhalation.
S 16 - Keep away from sources of ignition - No Smoking.
S 25 - Avoid contact with eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, 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:
oral-rat LD50  2140 ul/kg
American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.

intraperitoneal-mouse LD50  200 mg/kg
National Technical Information Service. Vol. AD691-490

intravenous-mouse LDLo  270 mg/kg
VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION CARDIAC: CHANGE IN RATE
Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 236, Pg. 633, 1953.

Dermal Toxicity:
skin-rabbit LD50 1770 ul/kg
American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.

Inhalation Toxicity:
inhalation-rat LCLo 2800 ppm/4H
American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.

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Safety in Use Information:
Category: flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for 2-methyl cyclohexanone usage levels up to:
  0.5000 % in the fragrance concentrate.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.12 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 0.10 (μg/capita/day)
Structure Class: II
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: 19
Click here to view publication 19
 average usual ppmaverage maximum ppm
baked goods: 10.0000025.00000
beverages(nonalcoholic): 5.0000010.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: 50.00000100.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 5.0000010.00000
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: --
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: 25.0000050.00000
soups: --
sugar substitutes: --
sweet sauces: --
Synonyms   Articles   Notes   Search   Top
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 51, (FGE.51)[1] - Consideration of alicyclic ketones and secondary alcohols and related esters evaluated by JECFA (59th meeting) and structurally related to alicyclic ketones, secondary alcohols and related esters evaluated by EFSA in FGE.09 (2004) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 51, Revision 1 (FGE.51Rev1): Consideration of alicyclic ketones and secondary alcohols and related esters evaluated by the JECFA (59th meeting) structurally related to alicyclic ketones secondary alcohols and related esters in FGE.09Rev3 (2011)
View page or View pdf
Flavouring Group Evaluation 51, Revision 2 (FGE.51Rev2): Consideration of alicyclic ketones and secondary alcohols and related esters evaluated by JECFA (59th meeting) structurally related to alicyclic ketones secondary alcohols and related esters in FGE.09Rev6 (2015)
View page or View pdf
EPI System: View
NIOSH Pocket Guide: search
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA Substance Registry Services (TSCA): 583-60-8
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 11419
National Institute of Allergy and Infectious Diseases: Data
WISER: UN 2297
WGK Germany: 1
 2-methylcyclohexan-1-one
Chemidplus: 0000583608
EPA/NOAA CAMEO: hazardous materials
RTECS: GW1750000 for cas# 583-60-8
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References:
 2-methylcyclohexan-1-one
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 583-60-8
Pubchem (cid): 11419
Pubchem (sid): 134978234
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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): HMDB31539
FooDB: FDB008147
Export Tariff Code: 2914.29.5000
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
Synonyms   Articles   Notes   Search   Top
Potential Blenders and core components note
 
For Odor
No odor group found for these
 camel grass oilFR
 cyclopentanoneFL/FR
 eucarvone 
 lippia alnifolia schau. leaf oil brazil 
laevo-monomenthyl glutarateFL/FR
laevo-menthyl methyl etherFL/FR
 pinocarvoneFL/FR
 satureja viminea oil costa rica 
 umbellulone 
aldehydic
isobutyraldehydeFL/FR
camphoreous
dextro-camphorFL/FR
 camphor tree bark oilFL/FR
 herbal ethanoneFR
 thujyl alcoholFL/FR
citrus
 ocimene quintoxideFL/FR
earthy
3-octanolFL/FR
 patchouli cyclohexanolFR
floral
 citronellal diisotridecyl acetalFR
 cyclohexyl ethyl acetateFL/FR
 cyclohexyl propanolFR
2-decalinolFR
 dihydrocarvyl acetateFL/FR
2',4'-dimethyl acetophenoneFL/FR
 earthy indaneFR
 floral methanolFR
 geranium oil chinaFL/FR
 menthadienyl formateFR
 muguet butanolFR
 ylang ylang flower oil CO2 extractFL/FR
 ylang ylang flower oil IFL/FR
 ylang ylang flower oil IIFL/FR
 ylang ylang flower oil IIIFL/FR
fruity
2-cyclopentyl cyclopentanoneFL/FR
 lilac lactoneFL/FR
green
 geranium absoluteFL/FR
 thiogeraniolFL/FR
 barosma betulina leaf oilFL/FR
1,4-cineoleFL/FR
 dehydroxylinalool oxideFL/FR
isodihydrolavandulolFR
(Z)-isodihydrolavandulyl acetateFR
 herbal undecanolFR
 hyssop oilFL/FR
trans-para-menthane-3,8-diol 
para-menthane-3,8-diolFL/FR
 myrtenolFL/FR
 perillaldehydeFL/FR
 pine hexanolFR
D-(+)-alpha-pineneFL/FR
 piperitoneFL/FR
 rosemary absoluteFL/FR
 rosemary oil moroccoFL/FR
 sabinene hydrateFL/FR
 viridiflorolFL/FR
licorice
sweet basil oleoresinFL/FR
mentholic
 cornmint oilFL/FR
 cornmint oil indiaFL/FR
 cornmint oil terpenelessFL/FR
(±)-mentholFL/FR
dextro-neomentholFL/FR
dextro,laevo-mentholFL/FR
laevo-mentholFL/FR
(±)-isomenthoneFL/FR
laevo-menthyl acetateFL/FR
 menthyl acetateFL/FR
 menthyl acetate racemicFL/FR
 peppermint cyclohexanoneFL/FR
dextro-piperitoneFL/FR
isopulegyl acetateFL/FR
minty
 agathosma crenulata leaf oilFL/FR
 camphene hydrate 
laevo-carveolFL/FR
laevo-carvoneFL/FR
 carvoneFL/FR
 carvyl propionateFL/FR
 cyclohexanoneFR
 dihydrocarveolFL/FR
 diosphenolFL/FR
bitter fennel seed oilFR
 mentha longifolia oilFR
dextro-2,8-para-menthadien-1-olFL/FR
trans-para-2,8-1-menthadienolFL/FR
trans-para-menthan-2-oneFL/FR
homomentholFL/FR
(-)-menthoneFL/FR
 menthoxypropane diolFL/FR
homomenthyl acetateFL/FR
 pennyroyal oilFL/FR
 pennyroyal oil spainFL/FR
 pennyroyal oil uruguayFL/FR
 peppermint oil CO2 extractFL/FR
 peppermint oil idahoFL/FR
 peppermint oil terpenelessFL/FR
 peppermint oil terpenesFR
beta-phellandreneFL/FR
 piperitenoneFL/FR
laevo-piperitoneFL/FR
isopropyl tiglateFL/FR
(-)-isopulegolFL/FR
isopulegoneFL/FR
(R)-(+)-pulegoneFR
isopulegyl formateFL/FR
 spearmint absoluteFL/FR
 spearmint oil americaFL/FR
 spearmint oil terpenelessFL/FR
 tetrahydrocarvoneFL/FR
 wintergreen oilFL/FR
 WS-23FL/FR
pine
 plectranthus glandulosus hook f. leaf oil cameroonFR
spicy
N,N-diethyl octanamideFR
laevo-verbenoneFL/FR
sulfurous
 buchu mercaptanFL/FR
thujonic
 armoise oilFR
tropical
beta-cyclocitralFL/FR
woody
para-tert-butyl cyclohexanoneFR
 
For Flavor
 
No flavor group found for these
 camphene hydrate 
 carvoneFL/FR
 cyclopentanoneFL/FR
2-cyclopentyl cyclopentanoneFL/FR
2',4'-dimethyl acetophenoneFL/FR
(±)-N,N-dimethyl menthyl succinamideFL
 eucarvone 
 lilac lactoneFL/FR
 limonen-10-yl acetateFL
 lippia alnifolia schau. leaf oil brazil 
dextro-2,8-para-menthadien-1-olFL/FR
cis+trans-para-1(7)8-menthadien-2-yl acetateFL
trans-para-2,8-1-menthadienolFL/FR
para-menthane-3,8-diolFL/FR
trans-para-menthane-3,8-diol 
3-laevo-menthoxy-2-methyl propane-1,2-diolFL
 menthoxypropane diolFL/FR
 menthyl acetate racemicFL/FR
laevo-monomenthyl glutarateFL/FR
laevo-menthyl methyl etherFL/FR
 menthyl propylene glycol carbonateFL
beta-phellandreneFL/FR
(Z,Z)-photocitral AFL
D-(+)-alpha-pineneFL/FR
 pinocarvoneFL/FR
 piperitenoneFL/FR
 piperitenone oxideFL
isopulegoneFL/FR
isopulegyl formateFL/FR
 satureja viminea oil costa rica 
 umbellulone 
laevo-verbenoneFL/FR
 viridiflorolFL/FR
 thujyl alcoholFL/FR
aldehydic
isobutyraldehydeFL/FR
camphoreous
 camphor tree bark oilFL/FR
coffee
2-isopropyl pyrazineFL
cooling
1,4-cineoleFL/FR
dextro,laevo-mentholFL/FR
laevo-mentholFL/FR
homomenthyl acetateFL/FR
 menthyl acetateFL/FR
 sabinene hydrateFL/FR
 WS-5FL
floral
 dihydrocarvyl acetateFL/FR
 geranium oil chinaFL/FR
 ylang ylang flower oil CO2 extractFL/FR
 ylang ylang flower oil IFL/FR
 ylang ylang flower oil IIFL/FR
 ylang ylang flower oil IIIFL/FR
green
 cyclohexyl ethyl acetateFL/FR
 dihydrocarveolFL/FR
 geranium absoluteFL/FR
 ocimene quintoxideFL/FR
isopropyl tiglateFL/FR
 thiogeraniolFL/FR
herbal
2-acetoxy-1,8-cineoleFL
 barosma betulina leaf oilFL/FR
 hyssop oilFL/FR
 rosemary absoluteFL/FR
 rosemary oil moroccoFL/FR
licorice
sweet basil oleoresinFL/FR
meaty
2-methyl 3-(methyl thio) furanFL
medicinal
dextro-camphorFL/FR
mentholic
 cornmint oilFL/FR
 cornmint oil terpenelessFL/FR
dextro-neomentholFL/FR
(±)-mentholFL/FR
 peppermint cyclohexanoneFL/FR
minty
 agathosma crenulata leaf oilFL/FR
laevo-carveolFL/FR
laevo-carvoneFL/FR
 carvyl propionateFL/FR
 cornmint oil indiaFL/FR
 diosphenolFL/FR
trans-para-menthan-2-oneFL/FR
homomentholFL/FR
(±)-isomenthoneFL/FR
(-)-menthoneFL/FR
laevo-menthyl acetateFL/FR
 myrtenolFL/FR
 pennyroyal oilFL/FR
 pennyroyal oil spainFL/FR
 pennyroyal oil uruguayFL/FR
 peppermint oil CO2 extractFL/FR
 peppermint oil idahoFL/FR
 peppermint oil terpenelessFL/FR
laevo-piperitoneFL/FR
 piperitoneFL/FR
dextro-piperitoneFL/FR
(-)-isopulegolFL/FR
 spearmint absoluteFL/FR
 spearmint oil americaFL/FR
 spearmint oil terpenelessFL/FR
 tetrahydrocarvoneFL/FR
 wintergreen oilFL/FR
 WS-23FL/FR
musty
3-octanolFL/FR
spicy
 perillaldehydeFL/FR
sulfurous
 buchu mercaptanFL/FR
tropical
beta-cyclocitralFL/FR
woody
 dehydroxylinalool oxideFL/FR
isopulegyl acetateFL/FR
 
Synonyms   Articles   Notes   Search   Top
Potential Uses:
 cornmintFL/FR
 heatherFR
 herbalFR
 mintFR
 peppermintFR
Synonyms   Articles   Notes   Search   Top
Occurrence (nature, food, other): note
 wine
Search  Picture
Synonyms   Articles   Notes   Search   Top
Synonyms:
 cyclohexanone, 2-methyl-
 cyclohexanone, 2-methyl-, (±)-
 methyl anone
2-methyl cyclohexan-1-one
alpha-methyl cyclohexanone
o-methyl cyclohexanone
ortho-methyl cyclohexanone
2-methyl-1-cyclohexanone
2-methyl-cyclohexanone
2-methylcyclohexan-1-one
2-methylcyclohexanone
alpha-methylcyclohexanone
o-methylcyclohexanone
ortho-methylcyclohexanone
 sexton B
 tetrahydro-o-cresol
Synonyms   Articles   Notes   Search   Top
Articles:
PubMed: ω-Transaminases for the amination of functionalised cyclic ketones.
PubMed: Clathrates of TETROL: Further Aspects of the Selective Inclusion of Methylcyclohexanones in Their Energetically Unfavorable Axial Methyl Conformations.
PubMed: Changes in acaricidal potency by introducing functional radicals and an acaricidal constituent isolated from Schizonepeta tenuifolia.
PubMed: Oxorhenium complexes bearing the water-soluble tris(pyrazol-1-yl)methanesulfonate, 1,3,5-triaza-7-phosphaadamantane, or related ligands, as catalysts for Baeyer-Villiger oxidation of ketones.
PubMed: The Prins reaction using ketones: rationalization and application toward the synthesis of the portentol skeleton.
PubMed: New 3H-indole synthesis by Fischer's method. Part I.
PubMed: PREPARATION OF (S)-2-Allyl-2-methylcyclohexanone (Cyclohexanone, 2-methyl-2-(2-propen-1-yl)-, (2S)-).
PubMed: Synthesis, stereochemical identification, and selective inhibitory activity against human monoamine oxidase-B of 2-methylcyclohexylidene-(4-arylthiazol-2-yl)hydrazones.
PubMed: Evidence from mechanistic probes for distinct hydroperoxide rearrangement mechanisms in the intradiol and extradiol catechol dioxygenases.
PubMed: Biotransformation of (+/-)-2-methylcyclohexanone by fungi.
PubMed: High-performance liquid chromatographic separation of enantiomers and diastereomers of 2-methylcyclohexanone thiosemicarbazone, and determination of absolute configuration and configurational stability.
PubMed: Lithium hexamethyldisilazide-mediated enolizations: influence of chelating ligands and hydrocarbon cosolvents on the rates and mechanisms.
PubMed: Pseudomonad cyclopentadecanone monooxygenase displaying an uncommon spectrum of Baeyer-Villiger oxidations of cyclic ketones.
PubMed: Studies of the condensation of sulfones with ketones and aldehydes.
PubMed: Regio- and enantioselective Pd-catalyzed allylic alkylation of ketones through allyl enol carbonates.
PubMed: Spectral and magnetic studies on manganese(II), cobalt(II) and nickel(II) complexes with Schiff bases.
PubMed: Mixed crystals containing the dioxo complex [[Ph3SiO]2VO2]- and novel pentacoordinated oxoperoxo complex [[Ph3SiO]2VO(O2)]-: X-ray crystal structure and assessment as oxidation catalysts.
PubMed: Reaction of ketones with lithium hexamethyldisilazide: competitive enolizations and 1,2-additions.
PubMed: Lithium hexamethyldisilazide-mediated ketone enolization: the influence of hindered dialkyl ethers and isostructural dialkylamines on reaction rates and mechanisms.
PubMed: Lithium diisopropylamide-mediated lithiations of imines: insights into highly structure-dependent rates and selectivities.
PubMed: Ketone enolization by lithium hexamethyldisilazide: structural and rate studies of the accelerating effects of trialkylamines.
PubMed: Lithium hexamethyldisilazide/triethylamine-mediated ketone enolization: remarkable rate accelerations stemming from a dimer-based mechanism.
PubMed: Unfunctionalized, alpha-epimerizable nonracemic ketones and aldehydes can be accessed by crystallization-induced dynamic resolution of imines.
PubMed: Differential responses to odorant analogs after recovery from nerve transection.
PubMed: The Suzuki coupling reaction in the stereocontrolled synthesis of 9-cis-retinoic acid and its ring-demethylated analogues.
PubMed: Catalytic Meerwein-Pondorf-Verley reduction by simple aluminum complexes.
PubMed: Regulated workplace ketones and their interference in the PFBHA method for aldehydes.
PubMed: Catalytic enantioselective protonation of lithium enolates with chiral imides
PubMed: Microwave Spectrum of 2-Methylcyclohexanone.
PubMed: Determination of 6s-trans conformation of retinal chromophore in sensory rhodopsin I and phoborhodopsin.
PubMed: Carbonyl reductase activity exhibited by pig testicular 20 beta-hydroxysteroid dehydrogenase.
PubMed: alpha-Nitration of Ketones via Enol Silyl Ethers. Radical Cations as Reactive Intermediates in Thermal and Photochemical Processes.
PubMed: Structure of (+/-)-(2S,1'S)-2-[hydroxy(phenyl)methyl]-2-methylcyclohexanone, C14H1802.
PubMed: STEREOCHEMICAL ASPECTS OF THE METABOLISM OF THE ISOMERIC METHYLCYCLOHEXANOLS AND METHYLCYCLOHEXANONES.
PubMed: The reaction of phenylmagnesium bromide with 2-chloro-4-methylcyclohexanone.
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