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

2-methyl-3-buten-2-ol
3-buten-2-ol, 2-methyl-

Sponsors

Name:2-methylbut-3-en-2-ol
CAS Number: 115-18-4Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:204-068-4
FDA UNII:SH64HE46L9
Nikkaji Web:J65.753K
Beilstein Number:1698263
MDL:MFCD00004470
CoE Number:11794
XlogP3-AA:0.80 (est)
Molecular Weight:86.13390000
Formula:C5 H10 O
NMR Predictor:Predict (works with chrome or firefox)
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
FLAVIS Number:02.123 (Old)
DG SANTE Food Flavourings:02.123 2-methylbut-3-en-2-ol
FDA Mainterm: 2-METHYL-3-BUTEN-2-OL
FDA Regulation:
FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION
Subpart F--Flavoring Agents and Related Substances
Sec. 172.515 Synthetic flavoring substances and adjuvants.
 
Physical Properties:
Appearance:colorless clear liquid (est)
Assay: 98.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:0.81800 to 0.82700 @ 25.00 °C.
Pounds per Gallon - (est).: 6.807 to 6.881
Refractive Index:1.41300 to 1.41900 @ 20.00 °C.
Melting Point: -28.00 °C. @ 760.00 mm Hg
Boiling Point: 97.00 to 99.00 °C. @ 760.00 mm Hg
Vapor Pressure:22.938999 mm/Hg @ 25.00 °C. (est)
Flash Point: 56.00 °F. TCC ( 13.33 °C. )
logP (o/w): 0.892 (est)
Soluble in:
 alcohol
 water, 4.874e+004 mg/L @ 25 °C (est)
 water, 1.00E+06 mg/L @ 25 °C (exp)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Type: herbal
Odor Strength:medium ,
recommend smelling in a 10.00 % solution or less
herbal earthy oily
Odor Description:at 10.00 % in dipropylene glycol. herbal earthy oily
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: perfuming agents
 
Suppliers:
BASF
Dimethylvinylcarbinol
BOC Sciences
For experimental / research use only.
2-Methyl-3-buten-2-ol
EMD Millipore
For experimental / research use only.
2-Methyl-3-buten-2-ol
Penta International
2-METHYL-3-BUTEN-2-OL
Santa Cruz Biotechnology
For experimental / research use only.
2-Methyl-3-buten-2-ol
Sigma-Aldrich
2-Methyl-3-buten-2-ol, ≥98%
Odor: oily; herbaceous; earthy
Certified Food Grade Products
Synerzine
2-Methyl-3-buten-2-ol
TCI AMERICA
For experimental / research use only.
2-Methyl-3-buten-2-ol >97.0%(GC)
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 11 - Highly flammable.
R 22 - Harmful if swallowed.
R 36 - Irritating to 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 1800 mg/kg
(BASF, 1972)

unreported-mammal (species unspecified) LD50 435 mg/kg
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(5), Pg. 61, 1986.

intraperitoneal-mouse LD50 800 mg/kg
Indian Journal of Chemistry, Section B: Organic Chemistry, Including Medicinal Chemistry. Vol. 14, Pg. 449, 1976.

intraperitoneal-rat LD50 1315 mg/kg
Planta Medica. Vol. 48, Pg. 120, 1983.

Dermal Toxicity:
subcutaneous-mouse LD50 1680 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 161, 1955.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: flavor and fragrance agents
Recommendation for 2-methyl-3-buten-2-ol usage levels up to:
  0.0500 % in the fragrance concentrate.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.0012 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 3900 (μg/person/day)
Threshold of Concern:540 (μg/person/day)
Structure Class: II
 
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): 7.0000035.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 5.0000025.00000
Edible ices, including sherbet and sorbet (03.0): 10.0000050.00000
Processed fruit (04.1): 7.0000035.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 10.0000050.00000
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 5.0000025.00000
Bakery wares (07.0): 10.0000050.00000
Meat and meat products, including poultry and game (08.0): 2.0000010.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 2.0000010.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 5.0000025.00000
Foodstuffs intended for particular nutritional uses (13.0): 10.0000050.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 5.0000025.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 10.0000050.00000
Ready-to-eat savouries (15.0): 20.00000100.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 5.0000025.00000
 
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):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 18 (FGE.18): Aliphatic, alicyclic and aromatic saturated and unsaturated tertiary alcohols, aromatic tertiary alcohols and their esters from chemical group 6
View page or View pdf

Flavouring Group Evaluation 18, Revision 1 (FGE. 18 Rev1)[1] : Aliphatic, alicyclic and aromatic saturated and unsaturated tertiary alcohols, aromatic tertiary alcohols and their esters from chemical groups 6 and 8
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 90 (FGE.90): Consideration of Aliphatic, acyclic and alicyclic terpenoid tertiary alcohols and structurally related substances evaluated by JECFA (68th meeting)FGE.18Rev1 (2009)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 18, Revision 2 (FGE.18Rev2): Aliphatic, alicyclic and aromatic saturated and unsaturated tertiary alcohols, aromatic tertiary alcohols and their esters from chemical groups 6 and 8.
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 18, Revision 3 (FGE.18Rev3): Aliphatic, alicyclic and aromatic saturated and unsaturated tertiary alcohols, aromatic tertiary alcohols and their esters from chemical groups 6 and 8.
View page or View pdf

EPI System: View
EPA Substance Registry Services (TSCA):115-18-4
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :8257
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1987
WGK Germany:1
2-methylbut-3-en-2-ol
Chemidplus:0000115184
EPA/NOAA CAMEO:hazardous materials
RTECS:EM9472000 for cas# 115-18-4
 
References:
 2-methylbut-3-en-2-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:115-18-4
Pubchem (cid):8257
Pubchem (sid):134974718
Flavornet:115-18-4
Pherobase:View
 
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
CHEBI:View
HMDB (The Human Metabolome Database):HMDB33854
FooDB:FDB012034
Export Tariff Code:2905.29.9000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
 
Potential Blenders and core components note
For Odor
balsamic
bornyl formate
FL/FR
dextro-
fenchone
FL/FR
camphoreous
laevo-
fenchone
FL/FR
caramellic
maltyl isobutyrate
FL/FR
earthy
(Z)-4-
octen-1-ol
FL/FR
1-
octen-3-one
FL/FR
2-
octyl acetate
FL/FR
(E+Z)-2,4,8-
trimethyl-3,7-nonadien-2-ol
FL/FR
ethereal
iso
valeraldehyde propylene glycol acetal
FL/FR
floral
dihydro-alpha-ionone
FL/FR
geranium oil morocco
FL/FR
phenethyl acetate
FL/FR
fruity
ethyl 2-ethyl acetoacetate
FL/FR
2-
methyl butyl isovalerate
FL/FR
2-
nonanone
FL/FR
octyl butyrate
FL/FR
propyl isobutyrate
FL/FR
fungal
hydroxymethyl hexyl ethyl ketone
FL/FR
green
ethyl (E,Z)-2,4-decadienoate
FL/FR
heptanal dimethyl acetal
FL/FR
herbal
dimethyl cyclormol (IFF)
FR
geranium concrete
FL/FR
guava leaf oil cuba
FR
herbal ketone
FR
ilex paraguariensis leaf solid extract
FR
1-
octen-3-yl acetate
FL/FR
viridiflorol
FL/FR
mossy
oakmoss absolute
FL/FR
spicy
2-
octanol
FL/FR
sulfurous
buchu mercaptan
FL/FR
cassis pentanone
FL/FR
passiflora acetate
FL/FR
waxy
2-
tridecanone
FL/FR
For Flavor
No flavor group found for these
bornyl formate
FL/FR
hydroxymethyl hexyl ethyl ketone
FL/FR
1,5-
octadien-3-ol
FL
(Z)-4-
octen-1-ol
FL/FR
2-
octyl acetate
FL/FR
(E+Z)-2,4,8-
trimethyl-3,7-nonadien-2-ol
FL/FR
viridiflorol
FL/FR
berry
berry
dihydro-alpha-ionone
FL/FR
camphoreous
laevo-
fenchone
FL/FR
cheesy
methyl ketones
FL
2-
nonanone
FL/FR
cooling
dextro-
fenchone
FL/FR
earthy
1-
octen-3-one
FL/FR
fatty
2-
tridecanone
FL/FR
floral
geranium oil morocco
FL/FR
fruity
ethyl 2-ethyl acetoacetate
FL/FR
2-
methyl butyl isovalerate
FL/FR
propyl isobutyrate
FL/FR
iso
valeraldehyde propylene glycol acetal
FL/FR
green
cassis pentanone
FL/FR
ethyl (E,Z)-2,4-decadienoate
FL/FR
heptanal dimethyl acetal
FL/FR
oakmoss absolute
FL/FR
1-
octen-3-yl acetate
FL/FR
herbal
geranium concrete
FL/FR
oregano oleoresin
FL
honey
phenethyl acetate
FL/FR
jammy
maltyl isobutyrate
FL/FR
phenolic
propyl 2-furoate
FL
spicy
2-
octanol
FL/FR
sulfurous
buchu mercaptan
FL/FR
methyl 2-(methyl thio) butyrate
FL
methyl thiomethyl butyrate
FL
tropical
passiflora acetate
FL/FR
waxy
octyl butyrate
FL/FR
 
Potential Uses:
FRearth
FRherbal
 
Occurrence (nature, food, other):note
 bilberry fruit - 0.05 mg/kg
Search Trop Picture
 cabbage - trace ammount
Search Trop Picture
 cardamom - trace ammount
Search Trop Picture
 cherimoya - up to 0.05 mg/kg
Search Trop Picture
 coffee - up to 2.5 mg/kg
Search PMC Picture
 cranberry fruit - 0.1 mg/kg
Search Trop Picture
 currant black currant fruit - 0.6 mg/kg
Search Trop Picture
 hop
Search Trop Picture
 lavender oil
Search Trop Picture
 lemon verbena oil turkey @ 0.10%
Data GC Search Trop Picture
 mango fruit - 3.3 mg/kg
Search Trop Picture
 milk powdered milk - 0.003 mg/kg
Search PMC Picture
 papaya fruit - 0.002 mg/kg
Search Trop Picture
 passion fruit - up to 0.1 mg/kg
Search Trop Picture
 tea - 1 mg/kg
Search Trop Picture
 ylang ylang oil
Search Trop Picture
 ylang ylang oil @ 0.07%
Data GC Search Trop Picture
 ylang ylang oil CO2 extract @ 0.18%
Data GC Search Trop Picture
 
Synonyms:
 but-3-en-2-ol, 2-methyl-
3-buten-2-ol, 2-methyl-
 buten-3-ol, 3-methyl-
1-buten-3-ol, 3-methyl-
 carbavane
 dimethylacetylenecarbinol
1,1-dimethylallyl alcohol
a,a-dimethylallyl alcohol
1,1-dimethylpropynol
 dimethylvinylcarbinol
 dimethylvinylmethanol
3-hydroxy-3-methyl butene
3-hydroxy-3-methyl-1-butene
3-hydroxy-3-methylbutene
2-methyl but-3-en-2-ol
3-methyl-1-buten-3-ol
2-methyl-2-hydroxy-3-butene
2-methyl-3-buten-2-yl alcohol
2-methyl-3-butenol
2-methylbut-3-en-2-ol
isoprenyl alcohol
 vinyl dimethyl carbinol
 vinyldimethylcarbinol
 

Articles:

PubMed:Organosulfate and Nitrate Formation and Reactivity from Epoxides Derived from 2-Methyl-3-buten-2-ol.
PubMed:2-Methyl-3-buten-2-ol (MBO) synthase expression in Nostoc punctiforme leads to over production of phytols.
PubMed:Fabrication of magnetically recoverable catalysts based on mixtures of Pd and iron oxide nanoparticles for hydrogenation of alkyne alcohols.
PubMed:Observations and models of emissions of volatile terpenoid compounds from needles of ponderosa pine trees growing in situ: control by light, temperature and stomatal conductance.
PubMed:Secondary Organic Aerosol Formation via 2-Methyl-3-buten-2-ol Photooxidation: Evidence of Acid-Catalyzed Reactive Uptake of Epoxides.
PubMed:Engineering an isoprenoid pathway in Escherichia coli for production of 2-methyl-3-buten-2-ol: a potential biofuel.
PubMed:Analysis and sensory evaluation of jostaberry (Ribes x nidigrolaria Bauer) volatiles.
PubMed:Emissions of putative isoprene oxidation products from mango branches under abiotic stress.
PubMed:Molecular simulations of green leaf volatiles and atmospheric oxidants on air/water interfaces.
PubMed:Monolithic poly (SPE-co-BVPE) capillary columns as a novel hydrophilic interaction liquid chromatography stationary phase for the separation of polar analytes.
PubMed:The sedative effects of hops (Humulus lupulus), a component of beer, on the activity/rest rhythm.
PubMed:Organosulfates as tracers for secondary organic aerosol (SOA) formation from 2-methyl-3-buten-2-ol (MBO) in the atmosphere.
PubMed:The sedative effect of non-alcoholic beer in healthy female nurses.
PubMed: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.
PubMed:Quenching of the triplet state of Safranine-O by aliphatic amines in AOT reverse micelles studied by transient absorption spectroscopy.
PubMed:Palladium-catalyzed mono-N-allylation of unprotected anthranilic acids with allylic alcohols in aqueous media.
PubMed:Determination and stability of CP-31398 in plasma from experimental animals by LC-MS/MS.
PubMed:Attraction modulated by spacing of pheromone components and anti-attractants in a bark beetle and a moth.
PubMed:Structure sensitivity of alkynol hydrogenation on shape- and size-controlled palladium nanocrystals: which sites are most active and selective?
PubMed:Encecalol angelate, an unstable chromene from Ageratum conyzoides L.: total synthesis and investigation of its antiprotozoal activity.
PubMed:Host resistance elicited by methyl jasmonate reduces emission of aggregation pheromones by the spruce bark beetle, Ips typographus.
PubMed:Biochemical characterization and homology modeling of methylbutenol synthase and implications for understanding hemiterpene synthase evolution in plants.
PubMed:A free-energy perturbation method based on Monte Carlo simulations using quantum mechanical calculations (QM/MC/FEP method): application to highly solvent-dependent reactions.
PubMed:The uptake of 2-methyl-3-buten-2-ol into aqueous mixed solutions of sulfuric acid and hydrogen peroxide.
PubMed:Preparation of glutathione imprinted polymer.
PubMed:Identification and field activity of a male-produced aggregation pheromone in the pine sawyer beetle, Monochamus galloprovincialis.
PubMed:Kinetics and mechanism of chlorine-atom-initiated oxidation of allyl alcohol, 3-buten-2-ol, and 2-methyl-3-buten-2-ol.
PubMed:Fragrance material review on 2-methyl-3-buten-2-ol.
PubMed:Isomer-selective study of the OH initiated oxidation of isoprene in the presence of O(2) and NO. I. The minor inner OH-addition channel.
PubMed:Photooxidation of 2-methyl-3-Buten-2-ol (MBO) as a potential source of secondary organic aerosol.
PubMed:Aggregation pheromone of the Qinghai spruce bark beetle, Ips nitidus eggers.
PubMed:Specificity and redundancy in the olfactory system of the bark beetle Ips typographus: single-cell responses to ecologically relevant odors.
PubMed:Metasternal gland volatiles and sexual communication in the triatomine bug, Rhodnius prolixus.
PubMed:Electrophysiological and behavioral responses of Ips duplicatus to aggregation pheromone in Inner Mongolia, China: amitinol as a potential pheromone component.
PubMed:Experimental and theoretical studies of the kinetics of the reactions of OH and OD with 2-methyl-3-buten-2-ol between 300 and 415 K at low pressure.
PubMed:Peroxy and alkoxy radicals from 2-methyl-3-buten-2-ol.
PubMed:Enhanced enzyme activity and enantioselectivity of lipases in organic solvents by crown ethers and cyclodextrins.
PubMed:Preparation of detergent-lipase complexes utilizing water-soluble amphiphiles in single aqueous phase and catalysis of transesterifications in homogeneous organic solvents.
PubMed:Enhancement of enzyme activity and enantioselectivity by cyclopentyl methyl ether in the transesterification catalyzed by Pseudomonas cepacia lipase co-lyophilized with cyclodextrins.
PubMed:CYP 17 and CYP 19 inhibitors. Evaluation of fluorine effects on the inhibiting activity of regioselectively fluorinated 1-(Naphthalen-2-ylmethyl)imidazoles.
PubMed:Hydroxyaldehyde products from hydroxyl radical reactions of Z-3-hexen-1-ol and 2-methyl-3-buten-2-ol quantified by SPME and API-MS.
PubMed:Chemical composition of the essential oils of two Rhodiola species from Tibet.
PubMed:Field response of Ips paraconfusus, Dendroctonus brevicomis, and their predators to 2-methyl-3-buten-2-ol, a novel alcohol emitted by ponderosa pine.
PubMed:Ion trap mass spectrometry affords advances in the analytical and atmospheric chemistry of 2-hydroxy-2-methylpropanal, a proposed photooxidation product of 2-methyl-3-buten-2-Ol.
PubMed:Dose-dependent response and preliminary observations on attraction range of Ips typographus to pheromones at low release rates.
PubMed:Volatile components in aqueous essence and fresh fruit of Cucumis melo cv. Athena (muskmelon) by GC-MS and GC-O.
PubMed:Biosynthesis of 2-methyl-3-buten-2-ol emitted from needles of Pinus ponderosa via the non-mevalonate DOXP/MEP pathway of isoprenoid formation.
PubMed:Canopy level fluxes of 2-methyl-3-buten-2-ol, acetone, and methanol by a portable relaxed eddy accumulation system.
PubMed:Enzymatic synthesis of methylbutenol from dimethylallyl diphosphate in needles of Pinus sabiniana.
PubMed:A novel efficient enzyme-immobilization reaction on NH2 polymers by means of L-ascorbic acid.
PubMed:Characterization of a Pseudomonas putida allylic alcohol dehydrogenase induced by growth on 2-methyl-3-buten-2-ol.
PubMed:Murine cytochrome P4503A is induced by 2-methyl-3-buten-2-ol, 3-methyl-1-pentyn-3-ol(meparfynol), and tert-amyl alcohol.
PubMed:1H NMR spin-echo spectroscopy of human erythrocytes. Transformation of exogenous compounds.
PubMed:Volatiles released from individual spruce bark beetle entrance holes Quantitative variations during the first week of attack.
PubMed:Inhibition of attraction to aggregation pheromone by verbenone and ipsenol : Density regulation mechanisms in bark beetleIps typographus.
PubMed:Individual variation in aggregation pheromone content of the bark beetle,Ips typographus.
PubMed:Methylbutynol effectively replaces methylbutenol, a pheromone component ofIps typographus (L.) (Coleoptera: Scolytidae).
PubMed:Attraction to pheromone sources of different quantity, quality, and spacing: Density-regulation mechanisms in bark beetleIps typographus.
PubMed:Field response of spruce bark beetle,Ips typographus, to aggregation pheromone candidates.
PubMed:Quantitative variation of pheromone components in the spruce bark beetleIps typographus from different attack phases.
PubMed:[The sedative-hypnotic action of hops. 4. Pharmacology of the hop substance 2-methyl-3-buten-2-ol].
PubMed:[Detection of sedative-hypnotic active ingredients in hops. 5. Degradation of bitter acids to 2-methyl-3-buten-2-ol, a hop constituent with sedative-hypnotic activity].
PubMed:Antimalarials. 11. 2-Vinylogs of substituted 2-aryl-4-quinoline amino alcohols.
PubMed:The chemical structure of pemptoporphyrin.
 
Notes:
narcotic, sleep-producing principle from hops. Flavour ingredient. Present in ylang ylang, orange juice, lemon juice, pineapple and other fruits
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