We have found 46587 results matching your criteria.
Please wait while we search...
  1. 1.
    General Material Information
  2. 2.
    PhysChem Properties
  3. 3.
    Occurrences
  4. 4.
    Organoleptic Properties
  5. 5.
    Suppliers
  6. 6.
    Potential Uses
  7. 7.
    Regulatory & Documentation
  8. 8.
    Safety Information
  9. 9.
    Other Information
  10. 10.
    Blenders & Components
  11. 11.
    Literature & References

prenol

Chemical Structure

General Material Information

Preferred name prenol
Trivial Name 3-Methyl-2-buten-1-ol
Short Description vertenol (Grau)
Formula C5 H10 O
CAS Number 556-82-1
Deleted CAS Number 135146-66-6
FEMA Number 3647
Flavis Number 2.109
ECHA Number 209-141-4
FDA UNII 55MY0HM445
Nikkaji Number J11.528B
Beilstein Number 1633479
MDL MFCD00002916
COE Number 11795
xLogP3-AA 1.00 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 1200 3-methyl-2-buten-1-ol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 556-82-1 ; 3-METHYL-2-BUTEN-1-OL
Synonyms
  • but-2-en-1-ol, 3-methyl-
  • 2-buten-1-ol, 3-methyl-
  • dimethyl allyl alcohol
  • 3,3-dimethylallyl alcohol
  • 3-methyl but-2-en-1-ol
  • 3-methyl crotyl alcohol
  • 3-methyl-2-buten-1-ol
  • 2-methyl-2-buten-4-ol
  • 3-methyl-2-butene-1-ol
  • 3-methyl-2-butenol
  • 3-methyl-2-butenyl alcohol
  • 3-methylbut-2-en-1-ol
  • 3-methylcrotyl alcohol
  • prenol (3-methyl-2-buten-1-ol)
  • prenyl alcohol
  • vertenol (Grau)
  • 3-methylbut-2-en-1-ol
  • 2-Buten-1-ol, 3-methyl-
  • 3-Methyl-2-buten-1-ol
  • γ,γ-Dimethylallyl alcohol
  • 3-Methyl-2-butene-1-ol
  • 3-Methyl-2-butenyl alcohol
  • 3,3-Dimethylallyl alcohol
  • 3-Methyl-2-butenol
  • Dimethylallyl alcohol
  • 3-Methylcrotyl alcohol
  • 2-Methyl-2-buten-4-ol
  • NSC 158709
  • Isopent-2-en-1-ol
  • Isopentenol

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

Google Scholar Start search
Google Books Start search
Google Patents Start search
Perfumer & Flavorists Start search
EU Patents Start search
PubMeb Start search
NCBI Start search

Literature & References

3-methylbut-2-en-1-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:556-82-1
Pubchem (cid):11173
Pubchem (sid):134977054
Flavornet:556-82-1
Pherobase:View
Publications by PubMed
MEP Pathway-mediated isopentenol production in metabolically engineered Escherichia coli.
Secondary ion mass spectrometry imaging of Dictyostelium discoideum aggregation streams.
cis-Prenyltransferase atCPT6 produces a family of very short-chain polyisoprenoids in planta.
Metabolic signatures of triatomine vectors of Trypanosoma cruzi unveiled by metabolomics.
Metabolic engineering of Escherichia coli for high-specificity production of isoprenol and prenol as next generation of biofuels.
Antibacterial/antifungal activity and synergistic interactions between polyprenols and other lipids isolated from Ginkgo biloba L. leaves.
N,O-Nucleosides from ene reactions of nitrosocarbonyl intermediates with the 3-methyl-2-buten-1-ol.
Sugar availability modulates polyisoprenoid and phytosterol profiles in Arabidopsis thaliana hairy root culture.
Synthesis and NMR characterization of (Z,Z,Z,Z,E,E,ω)-heptaprenol.
Polyprenols from the needles of Taxus chinensis var. mairei.
Bacterial degradation of tert-amyl alcohol proceeds via hemiterpene 2-methyl-3-buten-2-ol by employing the tertiary alcohol desaturase function of the Rieske nonheme mononuclear iron oxygenase MdpJ.
Hepatoprotective effects of polyprenols from Ginkgo biloba L. leaves on CCl4-induced hepatotoxicity in rats.
Role of novel terpenes in transcutaneous permeation of valsartan: effectiveness and mechanism of action.
Configuration of polyisoprenoids affects the permeability and thermotropic properties of phospholipid/polyisoprenoid model membranes.
Fragrance material review on 3-methyl-2-buten-1-ol.
Separation of hydrophobic metabolites using monolithic silica column in high-performance liquid chromatography and supercritical fluid chromatography.
Complete (1)H and (13)C signal assignment of prenol-10 with 3D NMR spectroscopy.
Solid-phase organic synthesis of polyisoprenoid alcohols with traceless sulfone linker.
A strategy for position-selective epoxidation of polyprenols.
Tumor-specificity and type of cell death induced by vitamin K2 derivatives and prenylalcohols.
Characterization of a PRL protein tyrosine phosphatase from Plasmodium falciparum.
The search for polyprenols in dendroflora of Vietnam.
Analysis of ubiquinones, dolichols, and dolichol diphosphate-oligosaccharides by liquid chromatography-electrospray ionization-mass spectrometry.
Antidyslipidemic activity of polyprenol from Coccinia grandis in high-fat diet-fed hamster model.
The use of long-chain plant polyprenols as a means to modify the biological properties of new biodegradable polyurethane scaffolds for tissue engineering. A pilot study.
Alloprenols: novel alpha-trans-polyprenols of Allophylus caudatus.
Precise bacterial polyprenol length control fails in Saccharomyces cerevisiae.
A new approach for the asymmetric total synthesis of umbelactone.
Activity of Pichia pastoris alternative cis-prenyltransferase is correlated with proliferation of peroxisomes.
Separation of polyprenol and dolichol by monolithic silica capillary column chromatography.
Polyprenyl lipid synthesis in mammalian cells expressing human cis-prenyl transferase.
The occurrence of polyprenols in seeds and leaves of woody plants.
Light conditions alter accumulation of long chain polyprenols in leaves of trees and shrubs throughout the vegetation season.
A comprehensive classification system for lipids.
Sulfone and phosphinic acid analogs of decaprenolphosphoarabinose as potential anti-tuberculosis agents.
[Studies on purification of polyprenol from Ginkgo biloba L. leaves].
Analysis of the volatile aroma constituents of parental and hybrid clones of pepino (Solanum muricatum).
Proteins are polyisoprenylated in Arabidopsis thaliana.
Defects in the N-linked oligosaccharide biosynthetic pathway in a Trypanosoma brucei glycosylation mutant.
Heteromeric geranyl diphosphate synthase from mint: construction of a functional fusion protein and inhibition by bisphosphonate substrate analogs.
Photooxygenation of allylic alcohols: kinetic comparison of unfunctionalized alkenes with prenol-type allylic alcohols, ethers and acetates.
Chemical analysis of Ginkgo biloba leaves and extracts.
Protein farnesyltransferase and protein prenylation in Plasmodium falciparum.
A general stereocontrolled, convergent synthesis of oligoprenols that parallels the biosynthetic pathway.
Biosynthesis of a substituted cellulose from a mutant strain of Xanthomonas campestris.
[Synthesis of dolicyl- and polyprenyl sulfates].
[Mechanisms of action of aerosol preparations based on Abies siberica polyprenols in experimental influenza infection].
[Prophylactic efficacy of aerosol preparations based on Abies siberica polyprenols in experimental influenza infection].
Constituents of Pilocarpus trachylophus.
Rational design of enantioselective enzymes requires considerations of entropy.
High-resolution analysis of polyprenols by supercritical fluid chromatography.
Study on the biosynthesis of dolichol in yeast: recognition of the prenyl chain length in polyprenol reduction.
Polyprenols in hairy roots of Coluria geoides.
Incorporation of radiolabeled prenyl alcohols and their analogs into mammalian cell proteins. A useful tool for studying protein prenylation.
The diversity of polyprenol pattern in leaves of fruit trees belonging to Rosaceae and Cornaceae.
Nonglucosylated oligosaccharides are transferred to protein in MI8-5 Chinese hamster ovary cells.
Transfer of two oligosaccharides to protein in a Chinese hamster ovary cell B211 which utilizes polyprenol for its N-linked glycosylation intermediates.
Identification of Schizosaccharomyces pombe prenol as dolichol-16,17.
Reduced utilization of Man5GlcNAc2-P-P-lipid in a Lec9 mutant of Chinese hamster ovary cells: analysis of the steps in oligosaccharide-lipid assembly.
Prenylation of proteins in Trypanosoma brucei.
On the specific pattern of long chain polyprenols in green needles of Pinus mugo Turra.
6-O-alpha-L-Arabinopyranosyl-beta-D-glucopyranosides as aroma precursors from passion fruit.
Dolichyl phosphate, a potent inducer of apoptosis in rat glioma C6 cells.
Biosynthesis of isoprenoid compounds in cattle filarial parasite Setaria digitata.
Biosynthesis of membrane-derived oligosaccharides. Membrane-bound glucosyltransferase system from Escherichia coli requires polyprenyl phosphate.
Function of alpha-D-glucosyl monophosphorylpolyprenol in biosynthesis of cell wall teichoic acids in Bacillus coagulans.
The function of galactosyl phosphorylpolyprenol in biosynthesis of lipoteichoic acid in Bacillus coagulans.
Long-chain polyprenols in gymnosperm plants.
Prenol nomenclature. Recommendations 1986. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN).
Biosynthesis of poly(galactosylglycerol phosphate) in Bacillus coagulans.
Structure and functions of linkage unit intermediates in the biosynthesis of ribitol teichoic acids in Staphylococcus aureus H and Bacillus subtilis W23.
Total synthesis of chain-length-uniform dolichyl phosphates and their fitness to accept hexoses in the enzymatic formation of lipoglycans.
Biosynthesis of wall teichoic acids in Staphylococcus aureus H, Micrococcus varians and Bacillus subtilis W23. Involvement of lipid intermediates containing the disaccharide N-acetylmannosaminyl N-acetylglucosamine.
The occurrence and seasonal distribution of C50-C60-polyprenols and of C100-and similar long-chain polyprenols in leaves of plants.
Subcellular localization and substrate specificity of dolichol kinase from rat liver.
Biosynthesis of polysaccharides in Acetobacter xylinum. Sequential synthesis of a heptasaccharide diphosphate prenol.
Synthesis of mannosyl cellobiose diphosphate prenol in Acetobacter xylinum.
Paramagnetic isoprenoid carrier lipids. 1. Chemical synthesis and incorporation into model membranes.
Factors affecting glucosyl and mannosyl transfer to dolichyl monophosphate by liver cell-free preparations.
Glucolipids of Zea mays and Pisum sativum.
Mechanism of the isomerization of isopentenyl pyrophosphate in Rhodotorual rubra-1.
Incorporation of radioactive mevalonate into C50 and C55 phenols by Streptococcus mutans.
Identification of prenol intermediates of wall biosynthesis in growing cells of Lactobacillus plantarum.
The transfer of mannose from guanosine diphosphate mannose to dolichol phosphate and protein by pig liver endoplasmic reticulum.
Polyprenol phosphate as an acceptor of mannose from guanosine diphosphate mannose in Aspergillus niger.
Polyprenols of Aspergillus niger. Their characterization, biosynthesis and subcellular distribution.
Prenol phosphates and mannosyltransferases.
The characterization of undecaprenol of Lactobacillus plantarum.
The characterization and distribution of hexahydropolyprenyl esters in cultures of Aspergillus fumigatus Fresenius.
Testicular sterols. V. Preparation and partial purification of a microsomal prenol pyrophosphate pyrophosphohydrolase.

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
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C01390
HMDB (The Human Metabolome Database):HMDB30124
FooDB:FDB001927
Export Tariff Code:2905.29.9000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 86.133903503418
Specific gravity @ 25 °C
Pounds per Gallon 7.023 to 7.089
Refractive Index 1.438 to 1.448 @ 20 °C
Boiling Point 138 to 174°C @ 760 mm Hg
Vapor Pressure 2.384 mmHg @ 25 °C
Flash Point TCC Value 43.33 °C TCC
logP (o/w) 1.055 est
Solubility
alcohol Yes
water, 4.094e+004 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Fruity
fruity, green, lavender, fermented, yeasty, sweet, alcoholic
General comment At 100.00 %. fruity green lavender
Mosciano, Gerard P&F 16, No. 4, 45, (1991) Sweet, fruity, alcoholic with a green nuance
Flavor Type: Fruity
green, fruity
Mosciano, Gerard P&F 16, No. 4, 45, (1991) At 30.00 ppm. Green, fruity
Works particularly well in passion fruit and cranberry flavors. Green fruity

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 10 - Flammable.
R 22 - Harmful if swallowed.
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 16 - Keep away from sources of ignition - No Smoking.
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:
oral-rat LD50 810 mg/kg
Food and Cosmetics Toxicology. Vol. 17, Pg. 895, 1979.

Dermal Toxicity:
skin-rabbit LD50 3900 mg/kg
Food and Cosmetics Toxicology. Vol. 17, Pg. 895, 1979.

Inhalation Toxicity:
Not determined

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 prenol usage levels up to:
8.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 4.60 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 3.80 (μg/capita/day)
Threshold of Concern:1800 (μg/person/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: 12
Click here to view publication 12
average usual ppmaverage maximum ppm
baked goods: -3.00000
beverages(nonalcoholic): -1.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: -20.00000
condiments / relishes: --
confectionery froastings: -2.00000
egg products: --
fats / oils: --
fish products: --
frozen dairy: --
fruit ices: -1.50000
gelatins / puddings: -2.00000
granulated sugar: --
gravies: --
hard candy: -5.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: -2.00000
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: -2.50000
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 202: 3-Alkylated aliphatic acyclic alpha,beta-unsaturated aldehydes and precursors with or without additional double bonds from chemical subgroup 1.1.3 of FGE.19[1]
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 20, Revision 2 (FGE.20Rev2): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30
View page or View pdf

Flavouring Group Evaluation 72 (FGE.72): Consideration of aliphatic, branched-chain saturated and unsaturated alcohols, aldehydes, acids, and related esters evaluated by the JECFA (61st meeting) structurally related to branched- and straight-chain unsaturated carboxylic acids. Esters of these and straight-chain aliphatic saturated alcohols evaluated by EFSA in FGE.05Rev2 (2010)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 20, Revision 3(FGE.20Rev3): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 72, Revision 1 (FGE.72Rev1): Consideration of aliphatic, branched-chain saturated and unsaturated alcohols, aldehydes, acids, and related esters evaluated by the JECFA (61st meeting) structurally related to branched- and straight-chain unsaturated carboxylic acids, esters of these and straight-chain aliphatic saturated alcohols evaluated by EFSA in FGE.05Rev2
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 72, Revision 2 (FGE.72Rev2): consideration of aliphatic, branched-chain saturated and unsaturated alcohols, aldehydes, acids and related esters evaluated by JECFA (61st, 68th and 69th meetings) and structurally related to flavouring substances in FGE.05Rev3
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):556-82-1
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11173
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1987
WGK Germany:1
3-methylbut-2-en-1-ol
Chemidplus:0000556821
RTECS:EM9472500 for cas# 556-82-1