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

prenyl mercaptan
prenylthiol

Supplier Sponsors

Name:3-methylbut-2-ene-1-thiol
CAS Number: 5287-45-6Picture of molecule3D/inchi
FDA UNII:FDG262156U
Nikkaji Web:J534.118C
MDL:MFCD00068639
CoE Number:11511
XlogP3-AA:2.00 (est)
Molecular Weight:102.19970000
Formula:C5 H10 S
NMR Predictor:Predict (works with chrome or firefox)
Category: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:522 prenylthiol
FLAVIS Number:12.170 (Old)
DG SANTE Food Flavourings:12.170 3-methylbut-2-ene-1-thiol
FEMA Number:3896 prenylthiol
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm: PRENYLTHIOL
 
Physical Properties:
Appearance:colorless clear liquid (est)
Assay: 98.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:0.88400 to 0.88500 @ 25.00 °C.
Pounds per Gallon - (est).: 7.356 to 7.364
Refractive Index:1.48300 to 1.49300 @ 20.00 °C.
Boiling Point: 128.00 to 135.00 °C. @ 760.00 mm Hg
Vapor Pressure:14.359000 mm/Hg @ 25.00 °C. (est)
Flash Point: 100.00 °F. TCC ( 37.78 °C. )
logP (o/w): 2.528 (est)
Soluble in:
 alcohol
 heptane
 triacetin
 water, 718.8 mg/L @ 25 °C (est)
Insoluble in:
 water
Similar Items:note
allyl mercaptan
amyl mercaptan
isoamyl mercaptan
sec-amyl mercaptan
tert-amyl mercaptan
benzyl mercaptan
buchu mercaptan
butyl mercaptan
isobutyl mercaptan
tert-butyl mercaptan
cetyl mercaptan
cyclohexyl mercaptan
cyclopentyl mercaptan
decyl mercaptan
dodecyl mercaptan
2-ethyl hexyl mercaptan
ethyl mercaptan
ethylene mercaptan
furfuryl mercaptan
grapefruit mercaptan
heptyl mercaptan
hexyl mercaptan
methyl mercaptan
2-naphthyl mercaptan
nonyl mercaptan
octyl mercaptan
peach mercaptan
1-phenethyl mercaptan
2-phenethyl mercaptan
phenyl mercaptan
propyl mercaptan
isopropyl mercaptan
2-thienyl mercaptan
3-thienyl mercaptan
tridecyl mercaptan
undecyl mercaptan
 
Organoleptic Properties:
Odor Type: sulfurous
Odor Strength:high ,
recommend smelling in a 0.10 % solution or less
sulfurous smoky leek onion skunk
Odor Description:at 0.10 % in propylene glycol. sulfurous smoke leek onion skunky
Odor and/or flavor descriptions from others (if found).
R C Treatt & Co Ltd
Prenyl mercaptan 1% Triacetin Kosher
Odor Description:Intense leek, onion-like, skunky
Frutarom
PRENYL MERCAPTAN 1% IN TRIACETIN
Odor Description:Burnt, Roast
Suggested Uses: Coffee, Savoury
 
Cosmetic Information:
None found
 
Suppliers:
Axxence Aromatic
PRENYL MERCAPTAN, Natural, Kosher
Sustainability
BOC Sciences
For experimental / research use only.
3-Methyl-2-buten-1-thiol > 95%
Charkit Chemical
PRENYL MERCAPTAN 1% IN TRIACETIN FEMA 3896
Frutarom
PRENYL MERCAPTAN 1% IN TRIACETIN
Odor: Burnt, Roast
Use: Suggested Uses: Coffee, Savoury
M&U International
PRENYLTHIOL, Kosher
Penta International
PRENYL MERCAPTAN 1% IN TRIACETIN, Kosher
Penta International
PRENYL MERCAPTAN NATURAL 1% IN ETHYL ALCOHOL, Kosher
Penta International
PRENYL MERCAPTAN NATURAL 1% IN NEOBEE, Kosher
Penta International
PRENYL MERCAPTAN NATURAL 1% IN PROPYLENE GLYCOL, Kosher
Penta International
PRENYL MERCAPTAN NATURAL 1% IN TRIACETIN, Kosher
Penta International
PRENYL MERCAPTAN, Kosher
R C Treatt & Co Ltd
Prenyl mercaptan 1% Triacetin
Kosher
Odor: Intense leek, onion-like, skunky
Taytonn
Prenyl Mercaptan (1% In TAC)
Taytonn
Prenyl Mercaptan
Odor: Burnt, Roast
TCI AMERICA
For experimental / research use only.
3-Methyl-2-butene-1-thiol >95.0%(T)
WholeChem
Prenylthiol
 
Safety Information:
European information :
Most important hazard(s):
Xi - Irritant
R 10 - Flammable.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 16 - Keep away from sources of ignition - No Smoking.
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 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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: flavoring agents
Recommendation for prenyl mercaptan usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): ND (μg/capita/day)
Structure Class: I
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: 18
 average usual ppmaverage maximum ppm
baked goods: 0.050005.00000
beverages(nonalcoholic): 0.001005.00000
beverages(alcoholic): 0.005000.05000
breakfast cereal: 0.010005.00000
cheese: --
chewing gum: 0.050000.10000
condiments / relishes: --
confectionery froastings: 0.010000.05000
egg products: --
fats / oils: --
fish products: --
frozen dairy: 0.100005.00000
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: 0.100005.00000
hard candy: 0.010000.05000
imitation dairy: --
instant coffee / tea: 0.001000.01000
jams / jellies: --
meat products: 0.010005.00000
milk products: 0.005005.00000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 0.200002.00000
snack foods: --
soft candy: 0.100005.00000
soups: 0.100005.00000
sugar substitutes: --
sweet sauces: 0.100005.00000
 
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 8 (FGE.08)[1]: Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical group 20
View page or View pdf

Flavouring Group Evaluation 8, Revision 1 (FGE.08Rev1): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 8, Revision 3 (FGE.08Rev3): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 08, Revision 4 (FGE.08Rev4): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30
View page or View pdf

EPI System: View
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :146586
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 3336
WGK Germany:3
3-methylbut-2-ene-1-thiol
Chemidplus:0005287456
 
References:
 3-methylbut-2-ene-1-thiol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):146586
Pubchem (sid):135103905
Flavornet:5287-45-6
 
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 Everything Added to Food in the United States (EAFUS):View
HMDB (The Human Metabolome Database):HMDB31529
FooDB:FDB008136
YMDB (Yeast Metabolome Database):YMDB01604
Export Tariff Code:2930.90.8599
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
FAO:Prenylthiol
 
Potential Blenders and core components note
For Odor
balsamic
guaiacyl phenyl acetate
FL/FR
chocolate
vanillyl ethyl ether
FL/FR
coffee
furfuryl mercaptan
FL/FR
fruity
ethyl 3-hydroxyhexanoate
FL/FR
green
3,7-
dimethyl-6-octenoic acid
FL/FR
leathery
castoreum absolute
FL/FR
phenolic
2,3-
dimethyl benzofuran
FL/FR
ortho-
guaiacol
FL/FR
4-
methyl-2,6-dimethoxyphenol
FL/FR
2-
propyl phenol
FL/FR
2,5-
xylenol
FL/FR
smoky
birch tar oil
FL/FR
2,6-
dimethoxyphenol
FL/FR
alpha-
ethoxy-ortho-cresol
FL/FR
4-
ethyl phenol
FL/FR
pyroligneous acids
FL/FR
pyroligneous acids hickory
FL/FR
spicy
cubeb oil
FL/FR
4-
ethyl guaiacol
FL/FR
pepper tree berry oil
FL/FR
woody
guaiacyl acetate
FL/FR
For Flavor
No flavor group found for these
benzyl disulfide
FL
birch tar oil
FL/FR
alpha-
ethoxy-ortho-cresol
FL/FR
2-
heptane thiol
FL
1-
methyl pyrrole
FL
peanut dithiazine
FL
2-
propyl phenol
FL/FR
burnt
burnt
bacon dithiazine
FL
chemical
2,3-
dimethyl benzofuran
FL/FR
coffee
furfuryl mercaptan
FL/FR
floral
3,7-
dimethyl-6-octenoic acid
FL/FR
fruity
ethyl 3-hydroxyhexanoate
FL/FR
leathery
castoreum absolute
FL/FR
meaty
4-
allyl-2,6-dimethoxyphenol
FL
2,6-
dimethyl thiophenol
FL
ortho-
thioguaiacol
FL
medicinal
2,6-
dimethoxyphenol
FL/FR
musty
2,5-
xylenol
FL/FR
onion
2-
methyl-1,3-dithiolane
FL
phenolic
guaiacyl phenyl acetate
FL/FR
4-
methyl-2,6-dimethoxyphenol
FL/FR
rummy
vanillyl ethyl ether
FL/FR
savory
2,4,6-
triethyl tetrahydro-1,3,5-dithiazine
FL
smoky
4-
ethyl phenol
FL/FR
pyroligneous acids
FL/FR
pyroligneous acids hickory
FL/FR
dextro-
xylose
FL
spicy
chipotle chili oleoresin
FL
cubeb oil
FL/FR
pepper tree berry oil
FL/FR
woody
4-
ethyl guaiacol
FL/FR
ortho-
guaiacol
FL/FR
guaiacyl acetate
FL/FR
 
Potential Uses:
FLcoffee dark roast coffee
FLfish
FLgarlic roasted garlic
FLmeat
FLmeat grilled meat
 
Occurrence (nature, food, other):note
 beer
Search PMC Picture
 coffee
Search PMC Picture
 hop oil
Search Trop Picture
 
Synonyms:
 but-2-ene-1-thiol, 3-methyl-
2-butene-1-thiol, 3-methyl-
3-methyl but-2-ene-1-thiol
 methyl butene thiol
3-methyl-2-buten-1-thiol
3-methyl-2-butene-1-thiol
3-methyl-2-butenyl mercaptan
3-methylbut-2-ene-1-thiol
 prenyl mercaptan 1% in triacetin
 prenyl mercaptan natural 1% in triacetin
 prenyl thiol
 prenylthiol
 

Articles:

PubMed:Comparison of aroma-active volatiles and their sensory characteristics of mangosteen wines prepared by Saccharomyces cerevisiae with GC-olfactometry and principal component analysis.
PubMed:Comparison of aroma active and sulfur volatiles in three fragrant rice cultivars using GC-olfactometry and GC-PFPD.
PubMed:Dual lipidation of the brain-specific Cdc42 isoform regulates its functional properties.
PubMed:Identification of a novel prenyl and palmitoyl modification at the CaaX motif of Cdc42 that regulates RhoGDI binding.
PubMed:3-Methyl-2-butene-1-thiol: identification, analysis, occurrence and sensory role of an uncommon thiol in wine.
PubMed:Lipid and sulfur substituted prenylcysteine analogs as human Icmt inhibitors.
PubMed:Construction and evaluation of self-cloning bottom-fermenting yeast with high SSU1 expression.
PubMed:Structures of RabGGTase-substrate/product complexes provide insights into the evolution of protein prenylation.
PubMed:Dechalcogenative allylic selenosulfide and disulfide rearrangements: complementary methods for the formation of allylic sulfides in the absence of electrophiles. Scope, limitations, and application to the functionalization of unprotected peptides in aqueous media.
PubMed:Combinatorial synthesis and screening of novel odorants such as polyfunctional thiols.
PubMed:Spectrophotometric method for exploring 3-methyl-2-butene-1-thiol (MBT) formation in lager.
PubMed:Identification of the volatile component(s) causing the characteristic foxy odor in various cultivars of Fritillaria imperialis L. (Liliaceae).
PubMed:Individual palmitoyl residues serve distinct roles in H-ras trafficking, microlocalization, and signaling.
PubMed:Photoreceptor cGMP phosphodiesterase delta subunit (PDEdelta) functions as a prenyl-binding protein.
PubMed:Protein farnesyltransferase inhibitors.
PubMed:Intein-mediated synthesis of geranylgeranylated Rab7 protein in vitro.
PubMed:Characterization of hydrophobic prenyl groups of isoprenylated proteins in human cancer cells.
PubMed:Model studies on the influence of coffee melanoidins on flavor volatiles of coffee beverages.
PubMed:Binding of the delta subunit to rod phosphodiesterase catalytic subunits requires methylated, prenylated C-termini of the catalytic subunits.
PubMed:Evidence for the carboxyl methylation of nuclear lamin-B in the pancreatic beta cell.
PubMed:Stringent structural requirements for anti-Ras activity of S-prenyl analogues.
PubMed:Isolation and characterization of a prenylcysteine lyase from bovine brain.
PubMed:Lipoconjugates: structure-activity studies for pheromone analogues of Ustilago maydis with varied lipophilicity.
PubMed:A mechanism for posttranslational modifications of proteins by yeast protein farnesyltransferase.
PubMed:Oxidative activation of the propolis hapten isoprenyl caffeate.
PubMed:Synthetic prenylated peptides: studying prenyl protein-specific endoprotease and other aspects of protein prenylation.
PubMed:Development of hydrophobicity parameters for prenylated proteins.
PubMed:Isopentenoid synthesis in embryonic Drosophila cells: prenylated protein profile and prenyl group usage.
PubMed:Quantitation of prenylcysteines by a selective cleavage reaction.
PubMed:Significance of C-terminal cysteine modifications to the biological activity of the Saccharomyces cerevisiae a-factor mating pheromone.
PubMed:Mass spectrometric signature of S-prenylated cysteine peptides.
PubMed:Brain G protein gamma subunits contain an all-trans-geranylgeranylcysteine methyl ester at their carboxyl termini.
PubMed:Prenylated proteins: demonstration of a thioether linkage to cysteine of proteins.
 
Notes:
Substance responsible for ``sun-struck'' flavour of beer. Found in coffee. Used in food flavourings
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