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2,3-Hexanedione

HCID 19707
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
3848-24-6
Standard SMILES
CCCC(=O)C(C)=O
InChIKey
MWVFCEVNXHTDNF-UHFFFAOYSA-N
Molecular formula
C6H10O2
Average molar mass
114.14 g/mol
Monoisotopic mass
114.06807956

Overview

2,3-hexanedione is a yellow liquid. Sharp penetrating odor in high concentrations. Sweet, aromatic odor when diluted. (NTP, 1992)

Names & identifiers

Preferred name
2,3-Hexanedione
IUPAC
hexane-2,3-dione
English name
2,3-HEXANEDIONE
Molecular formula
C6H10O2
Molecular weight
114.14

Names & synonyms

2,3-HEXANEDIONE3848-24-6hexane-2,3-dioneAcetylbutyrylAcetyl butyrylMethyl propyl diketoneFEMA No. 2558DTXSID2047066559ANR3NVSNSC-31665DTXCID0027066CHEBI:87583
Show more names
FEMA 2558Hexan-2,3-dionmethylpropyldiketonePropylmethyl diketone2 3-HEXANEDIONE 90+%
RefChem:81914223-350-8HexanedioneButyryl acetyl2,3-hexandione2,3-HexanodioneMethyl propyl glyoxalMFCD00009398

Database identifiers

CAS
3848-24-6
PubChem CID
19707
DTXSID
DTXSID2047066
ChEMBL
CHEMBL3187497
ChEBI
CHEBI:87583
UNII
559ANR3NVS
EC Number
223-350-8
Nikkaji
J64.761F

Properties

Computed structural properties

XLogP
0.4
Topological polar surface area
34.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
3
Heavy atoms
8
Formal charge
0
Complexity
105

Experimental & physicochemical properties

LipidsFatty Acyls [FA] -> Oxygenated hydrocarbons [FA12]
SpringerMaterials PropertiesOptical coefficient
FragrancesFragrance Ingredient (2,3-Hexanedione) -> IFRA transparency List
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 2 items

0.934 at 66 °F (NTP, 1992) - Less dense than water; will float

0.930-0.950

Flavoring AgentsEU Flavoring substances
Solubility · 4 items

less than 1 mg/mL at 72 °F (NTP, 1992)

slightly

slightly soluble in water; soluble in propylene glycol, alcohol, and oils

(in ethanol)

Flash Point83 °F (NTP, 1992)
Boiling Point · 3 items

262 °F at 760 mmHg (NTP, 1992)

128.00 °C. @ 760.00 mm Hg

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1508 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: 2,3-Hexanedione

2,3-Hexanedione: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelFlammable Liquid
Fire HazardsThis chemical is flammable. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound include irritation of the skin, eyes, mucous membranes and upper respiratory tract.
Reactive GroupKetones
Reactivity AlertsHighly Flammable
Reactivity Profile2,3-HEXANEDIONE is incompatible with strong oxidizing agents and strong bases. (NTP, 1992)
Air and Water ReactionsHighly flammable. Insoluble in water.

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

Use Classification · 4 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information2,3-Hexanedione: ACTIVE
Applications · 5 items

Description2,3-Hexanedione has a powerful, creamy, sweet, and buttery odor (less than diacetyl) and a buttery, cheese taste. It may be synthesized from propionyl aldehyde condensed over ethyl acetylacetate;the resulting product is then oxidized (H2O2 and sodium tungstate), hydrolyzed, and finally decarboxylated to 2,3-hexanedione; from methyl butyl ketone and ethyl propyl ketone by way of the monoxime; also from acetoxy mesityl oxide.

OccurrenceReported found in fermented soybean, peach, roasted chicken, beer, coffee, shoyu and clam.

Uses2,3-Hexanedione is used to evaluate the influence of xanthan concentration on the release of aroma compounds in xanthan-thickened food model systems. It reacts with ethylenediamine to yield macrocyclic tetradentate 12-membered nitrogen donor (N4) ligand.

Uses2,3-Hexanedione was used to evaluate the influence of xanthan concentration on the release of aroma compounds in xanthan-thickened food model systems.

General DescriptionYellow liquid. Sharp penetrating odor in high concentrations. Sweet, aromatic odor when diluted.

Preparation methods · 1 item

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Related reactions

1 records
New reaction record
HRID 1296732 reaction equation
HRID 1296732As reactantuspto-grants-2007_07

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

128 °C

Melting Point-30.00 °C. @ 760.00 mm Hg
Vapor Pressure0.5 mmHg at 84 °F ; 19.0 mmHg at 124 °F (NTP, 1992)
Refractive Index1.409-1.419

Physicochemical properties

Melting point
-30 °C · -30 °C
Boiling point
128 °C · 128 °C(lit.)
Density
0.934 g/mL · 0.934 g/mL at 25 °C(lit.)
vapor density
3.9 · 3.9 (vs air)
vapor pressure
10 mm · 10 mm Hg ( 20 °C)
refractive index
20 · n20/D 1.412(lit.)
FEMA
2558 · 2558 | 2,3-HEXANEDIONE
FLAVIS Number
7.018 · 07.018 | Hexan-2,3-dione
Flash point
83 °F · 83 °F
storage temp.
30 °C · Store below +30°C.
solubility
2 O: · H2O: soluble (slightly soluble)
form
liquid
Appearance
Light yellow to yellow Liquid
Odor
1 % · at 1.00 % in dipropylene glycol. dry sweet caramel butter oily fatty creamy phenolic fruity
Odor Type
buttery
explosive limit
1.2 · 1.2-5.9%(V)
biological source
synthetic
Water Solubility
Partly miscible in water.
JECFA Number
412 · 412
BRN
1699896 · 1699896
Stability
Stable. Flammable. Incompatible with strong bases, strong oxidizing agents.
Major Application
flavors and fragrances
Cosmetics Ingredients Functions
PERFUMING
InChI
1S/C6H10O2/c1-3-4-6(8)5(2)7/h3-4H2,1-2H3
InChIKey
MWVFCEVNXHTDNF-UHFFFAOYSA-N
SMILES
CCCC(=O)C(C)=O
LogP
-0.27 · -0.27
CAS DataBase Reference
3848 · 3848-24-6(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS)
2 · 2,3-HEXANEDIONE
EWG's Food Scores
1 · 1
FDA UNII
559 ANR3NVS · 559ANR3NVS
EPA Substance Registry System
2 · 2,3-Hexanedione (3848-24-6)
UNSPSC Code
85151701 · 85151701
NACRES
24 · NA.24
Symbol(GHS)
2 · GHS02,GHS08
Signal word
Warning
Hazard statements
226 · H226-H373
Precautionary statements
210 · P210-P233-P240-P241-P242-P314
target organs
Respiratory system
Hazard Codes
Xi
Risk Statements
10 · 10-36/37/38
Safety Statements
26 · 26-36/37/39-16
RIDADR
1224 · UN 1224 3/PG 3
WGK Germany
2 · 2
RTECS
3140000 · MO3140000
Autoignition Temperature
245 °C · 245 °C
TSCA
TSCA listed
HazardClass
3 · 3
PackingGroup
III
HS Code
29141990 · 29141990
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
3 STOT · Flam. Liq. 3STOT RE 2 Inhalation
Toxicity
50 orally · LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 5000 mg/kg
Limited Quantities
5 L · 5.0 L (1.3 gallons) (liquid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazard Classes and Categories
Flam. Liq. 3 (100%)

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Isolation and EvacuationExcerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:
Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Safety data

wgk
2
tsca
TSCA listed
rtecs
MO3140000
ridadr
UN 1224 3/PG 3
hs_code
29141990
Toxicity
LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 5000 mg/kg
risk_code
10-36/37/38
Signal word
Warning
Symbol(GHS)
GHS02,GHS08
hazard_code
Xi
safety_code
26-36/37/39-16
hazard_class
3
Storage Class
3 - Flammable liquids
packing_group
III
target organs
Respiratory system
Hazard statements
H226-H373
Limited Quantities
5.0 L (1.3 gallons) (liquid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazard Classifications
Flam. Liq. 3STOT RE 2 Inhalation
Autoignition Temperature
245 °C
Precautionary statements
P210-P233-P240-P241-P242-P314

PreparationFrom propionyl aldehyde condensed over ethyl acetylacetate; the resulting product is then oxidized (H2O2 and sodium tungstate), hydrolyzed and finally decarboxylated to 2,3-dexanedione; from methyl butyl ketone and ethyl propyl ketone by way of the monoxime; also from acetoxy mesityl oxide

Upstream & downstream products

Upstream raw materials

2-HexanoneSodium tungstate dihydrate

Downstream products

2-methyl-3-isobutylpyrazine

Additional notes

DefinitionChEBI: An alpha-diketone that is hexane substituted by oxo groups at positions 2 and 3 respectively.