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prenyl mercaptan

Chemical Structure

General Material Information

Preferred name prenyl mercaptan
Trivial Name 3-Methyl-2-butene-1-thiol
Short Description prenylthiol
Formula C5 H10 S
CAS Number 5287-45-6
FEMA Number 3896
Flavis Number 12.17
FDA UNII FDG262156U
Nikkaji Number J534.118C
MDL MFCD00068639
COE Number 11511
xLogP3-AA 2.00 (est)
NMR Predictor External link
JECFA Food Flavoring 522 prenylthiol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 5287-45-6 ; PRENYLTHIOL
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
  • 3-methylbut-2-ene-1-thiol
  • 2-Butene-1-thiol, 3-methyl-
  • 3-Methyl-2-butene-1-thiol
  • MBT
  • 3-Methyl-1-mercapto-2-butene
  • 3-Methyl-2-buten-1-thiol

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

3-methylbut-2-ene-1-thiol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):146586
Pubchem (sid):135103905
Flavornet:5287-45-6
Publications by PubMed
Comparison of aroma-active volatiles and their sensory characteristics of mangosteen wines prepared by Saccharomyces cerevisiae with GC-olfactometry and principal component analysis.
Comparison of aroma active and sulfur volatiles in three fragrant rice cultivars using GC-olfactometry and GC-PFPD.
Dual lipidation of the brain-specific Cdc42 isoform regulates its functional properties.
Identification of a novel prenyl and palmitoyl modification at the CaaX motif of Cdc42 that regulates RhoGDI binding.
3-Methyl-2-butene-1-thiol: identification, analysis, occurrence and sensory role of an uncommon thiol in wine.
Lipid and sulfur substituted prenylcysteine analogs as human Icmt inhibitors.
Construction and evaluation of self-cloning bottom-fermenting yeast with high SSU1 expression.
Structures of RabGGTase-substrate/product complexes provide insights into the evolution of protein prenylation.
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.
Combinatorial synthesis and screening of novel odorants such as polyfunctional thiols.
Spectrophotometric method for exploring 3-methyl-2-butene-1-thiol (MBT) formation in lager.
Identification of the volatile component(s) causing the characteristic foxy odor in various cultivars of Fritillaria imperialis L. (Liliaceae).
Individual palmitoyl residues serve distinct roles in H-ras trafficking, microlocalization, and signaling.
Photoreceptor cGMP phosphodiesterase delta subunit (PDEdelta) functions as a prenyl-binding protein.
Protein farnesyltransferase inhibitors.
Intein-mediated synthesis of geranylgeranylated Rab7 protein in vitro.
Characterization of hydrophobic prenyl groups of isoprenylated proteins in human cancer cells.
Model studies on the influence of coffee melanoidins on flavor volatiles of coffee beverages.
Binding of the delta subunit to rod phosphodiesterase catalytic subunits requires methylated, prenylated C-termini of the catalytic subunits.
Evidence for the carboxyl methylation of nuclear lamin-B in the pancreatic beta cell.
Stringent structural requirements for anti-Ras activity of S-prenyl analogues.
Isolation and characterization of a prenylcysteine lyase from bovine brain.
Lipoconjugates: structure-activity studies for pheromone analogues of Ustilago maydis with varied lipophilicity.
A mechanism for posttranslational modifications of proteins by yeast protein farnesyltransferase.
Oxidative activation of the propolis hapten isoprenyl caffeate.
Synthetic prenylated peptides: studying prenyl protein-specific endoprotease and other aspects of protein prenylation.
Development of hydrophobicity parameters for prenylated proteins.
Isopentenoid synthesis in embryonic Drosophila cells: prenylated protein profile and prenyl group usage.
Quantitation of prenylcysteines by a selective cleavage reaction.
Significance of C-terminal cysteine modifications to the biological activity of the Saccharomyces cerevisiae a-factor mating pheromone.
Mass spectrometric signature of S-prenylated cysteine peptides.
Brain G protein gamma subunits contain an all-trans-geranylgeranylcysteine methyl ester at their carboxyl termini.
Prenylated proteins: demonstration of a thioether linkage to cysteine of proteins.

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
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

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 102.19969940186
Specific gravity @ 25 °C
Pounds per Gallon 7.356 to 7.364
Refractive Index 1.483 to 1.493 @ 20 °C
Boiling Point 128 to 135°C @ 760 mm Hg
Vapor Pressure 14.359 mmHg @ 25 °C
Flash Point TCC Value 37.78 °C TCC
logP (o/w) 2.528 est
Solubility
alcohol Yes
heptane Yes
triacetin Yes
water, 718.8 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Sulfurous
sulfurous, smoky, leek, onion, skunk
General comment At 0.10 % in propylene glycol. sulfurous smoke leek onion skunky

Occurrences

Safety Information

Safety information

Preferred SDS: View
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
Click here to view publication 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
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
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