Grundinformationen
- Standard-SMILES
CCCCCC(C)=O- InChIKey
CATSNJVOTSVZJV-UHFFFAOYSA-N- Summenformel
- C7H14O
- Durchschnittliche Molmasse
- 114,19 g/mol
- Monoisotopische Masse
- 114,10446507
Überblick
N-amyl methyl ketone appears as a clear colorless liquid. Flash point 126 °F. Less dense than water and only slightly soluble in water. Hence floats on water. Vapors heavier than air. Density 6.8 lb / gal. Used as a synthetic flavoring and in perfumes.
Namen und Bezeichner
- Bevorzugter Name
- 2-Heptanone
- IUPAC
- heptan-2-one
- Lokaler Name
- 2-Heptanon
- Englischer Name
- 2-Heptanone
- Summenformel
- C7H14O
- Molmasse
- 114.19
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
110-43-0- PubChem CID
- 8051
- DTXSID
DTXSID5021916- ChEMBL
CHEMBL18893- ChEBI
CHEBI:5672- UNII
- 89VVP1B008
- EC Number
- 203-767-1
- Nikkaji
- J5.091A
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2
- Polarare Oberfläche (TPSA)
- 17,1 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 8
- Formalladung
- 0
- Komplexität
- 66,8
Experimentelle und physikochemische Eigenschaften
LogP
log Kow = 1.98
1.98
2.08
Odor
Penetrating fruity odor
CHARACTERISTIC BANANA, SLIGHTLY SPICY ODOR
Banana-like fruity odor
Density
0.82 (USCG, 1999) - Less dense than water; will float
0.8324 at 0 °C/4 °C; 0.8197 at 15 °C/4 °C; 0.8068 at 30 °C/4 °C
Bulk density = 6.8 lb/gal
Relative density (water = 1): 0.8
0.814-0.819
0.81
Physikochemische Eigenschaften
- Schmelzpunkt
- -35 °C · -35 °C (lit.)
- Siedepunkt
- 149 · 149-150 °C (lit.)
- Dichte
- 0.82 g/mL · 0.82 g/mL at 25 °C (lit.)
- Dampfdichte
- 3.94 · 3.94 (vs air)
- Dampfdruck
- 2.14 mm · 2.14 mm Hg ( 20 °C)
- Brechungsindex
- 20 · n20/D 1.408(lit.)
- FEMA
- 2544 · 2544 | 2-HEPTANONE
- Flammpunkt
- 106 °F · 106 °F
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- 4.21 g/L · water: soluble4.21 g/L at 20°C
- Aggregatzustand
- Liquid
- Farbe
- Clear colorless
- Geruch (Odor)
- 10 % · at 10.00 % in dipropylene glycol. fruity spicy sweet herbal coconut woody
- Geruchsart
- cheesy
- Biologische Quelle
- synthetic
- Odor Threshold
- 0.0068 ppm · 0.0068ppm
- Explosionsgrenze
- 1.11 · 1.11-7.9%(V)
- Wasserlöslichkeit
- 4.3 g/L · 4.3 g/L (20 ºC)
- Spezifische Wärmekapazität
- 2.04 J/ · Cp(liquid): 2.04 J/(g·K), at 25℃
- JECFA Number
- 283 · 283
- Merck
- 14 · 14,4663
- BRN
- 1699063 · 1699063
- Henry's Law Constant
- 3.59 at · 3.59 at 37 °C (static headspace-GC, Bylaite et al., 2004)
- Dielectric constant
- 12.9 · 12.9(22℃)
- Stabilität
- Stable. Flammable. Incompatible with strong oxidizing agents, strong reducing agents, strong bases.
- Major Application
- flavors and fragrances
- Kosmetik-Inhaltsstoffe Funktionen
- PERFUMING
- InChI
- 1S/C7H14O/c1-3-4-5-6-7(2)8/h3-6H2,1-2H3
- InChIKey
- CATSNJVOTSVZJV-UHFFFAOYSA-N
- SMILES
- CCCCCC(C)=O
- LogP
- 2.26 at · 2.26 at 30℃
- CAS Datenbank
- 110 · 110-43-0(CAS DataBase Reference)
- NIST chemische Informationen
- 2 · 2-Heptanone(110-43-0)
- EPA chemische Informationen
- 2 · 2-Heptanone (110-43-0)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H226: Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P303+P361+P353, P304+P340, P317, P330, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for < 0.1% (2 of 3241) of reports.
Warning
H226 (> 99.9%): Flammable liquid and vapor [Warning Flammable liquids]
Gefahrenhinweise
Regulatory Information
Chemical: 2-Heptanone
Regulation (EC) No 1831/2003 (amended)
2-Heptanone is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Heptanone are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 06-07-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/10230
2-Heptanone: HSNO Approval: HSR001084 Approved with controls
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon dioxide and carbon monoxide, may be formed when involved in fire.
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Flammable. Above 48 °C explosive vapour/air mixtures may be formed.
Health Hazards
Inhalation can cause headache, fatigue, nausea, vomiting, dizziness, stupor, drowsiness, disturbed vision, and unconsciousness. Skin contact can cause moderate irritation, defatting, and dermatitis. Ingestion may cause irritation of lips and mouth, gastro-intestinal irritation, nausea, diarrhea, drowsiness, loss of consciousness, weak and rapid pulse, cold-pale complexion. (USCG, 1999)
· Inhalation or contact with material may irritate or burn skin and eyes.
· Inhalation or contact with material may irritate or burn skin and eyes.
DOT ID and Guide
1110 127
1110 127
1110 127
FDA Requirements
2-Heptanone is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient. Synthetic flavoring substances and adjuvants /incl 2-Heptanone/ may be safely used in foods.
Sicherheit und Schutzausrüstung
Fire Fighting
Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:
Use AFFF, alcohol-resistant foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures
Fresh air, rest. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Rinse mouth.
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
Excerpt from NIOSH Pocket Guide for Methyl (n-amyl) ketone:
General First Aid:
General First Aid:
(General first aid procedures)
Exposure Control and Personal Protection
· Wear positive pressure self-contained breathing apparatus (SCBA).
· Wear positive pressure self-contained breathing apparatus (SCBA).
Disposal Methods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Spillage Disposal
Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Collect leaking and spilled liquid in sealable metal containers as far as possible. Absorb remaining liquid in dry sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer.
Preventive Measures
The basic ventilation methods are local exhaust ventilation and dilution or general ventilation.
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
Isolation and Evacuation
Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:
Immediate precautionary measure
Immediate precautionary measure
Toxikologische Informationen
Interactions
Chloroform-induced liver injury was evaluated in male rats pretreated (15 mmol/kg, orally) with 2-heptanone. After 18 hr, a challenging dose of chloroform (0.50 or 0.75 ml/kg ip) was given. Liver damage was evaluated 24 hr after chloroform admin by determining elevations in plasma glutamic-pyruvic transaminase and ornithine carbamyl transferase activity. 2-Heptanone potentiated chloroform-induced liver damage.
When methyl n-amyl ketone (456 mg/kg) was administered with equimolar doses of MnBK (methyl n-butyl ketone) by subcutaneous injection 5 days/week for 20 week, the neurotoxicity of MnBK, as measured by motor fiber conduction velocity and motor distal latency, was enhanced (p<0.01) ...
Chloroform (CHCl3)-induced hepato- and nephrotoxicity was evaluated in male, Fischer 344 rats pretreated with various dosages (1.0 to 15.0 mmol/kg, /orally/) of acetone (Ac), 2-butanone (Bu), 2-pentanone (Pn), 2-hexanone (Hx), or 2-heptanone (Hp). The CHCl3 challenge dosage (0.5 ml/kg, ip) produced slight centrilobular hydropic degeneration and patchy degeneration and necrosis in the proximal tubules of corn oil-pretreated rats. Each of the ketones studied produced a dose-related potentiation of CHCl3 liver and kidney injury. CHCl3 produced extensive tubular and centrilobular necrosis when administered to ketone-pretreated rats. The relationship between ketone dosage and the magnitude of the potentiated response was nonlinear. Maximum potentiation of CHCl3 toxicity occurred in the dosage range of 5.0 to 10.0 mmol ketone/kg. Ketone dosages greater than 10.0 mmol/kg were associated with a reduction in the degree of CHCl3 injury. At the lowest ketone dosage (1.0 mmol/kg), potentiating capacity appeared to be related to ketone carbon skeleton length. No differences in potentiating capacity were discernable between the ketones at dosages of 5.0 to 10.0 mmol/kg.
Ecotoxicity Values
LC50 Pimephales promelas (Fathead minnow) 131 mg/L/96 hr (confidence limit 126-137 mg/L), flow-through bioassay with measured concentrations, 24.2 °C, dissolved oxygen 7.2 mg/L, hardness 46.4 mg/L calcium carbonate, alkalinity 42.1 mg/L calcium carbonate, and pH 7.72.
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 280(SRC), determined from a log Kow of 1.98(2) and a regression-derived equation(3), indicates that 2-heptanone is expected to have moderate mobility in soil(SRC). Volatilization of 2-heptanone from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.69X10-4 atm-cu m/mole(4). 2-Heptanone is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.85 mm Hg(5). Screening studies indicate that 2-heptanone is likely to biodegrade in aquatic systems under aerobic conditions(6-9).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 280(SRC), determined from a log Kow of 1.98(2) and a regression-derived equation(3), indicates that 2-heptanone is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.69X10-4 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4.8 hours and 6 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 7(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Screening studies indicate that 2-heptanone is likely to biodegrade in aquatic systems under aerobic conditions(7-10).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-heptanone, which has a vapor pressure of 3.85 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-heptanone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.4 days(SRC), calculated from its rate constant of 1.17X10-11 cu cm/molecule-sec at 25 °C(3). Although 2-heptanone has the potential of being removed from the atmosphere by direct photochemical degradation(4), the rate of this process is not expected to be able to compete with atmospheric removal by the reaction with hydroxyl radicals(SRC).
Food Survey Values
2-Heptanone was detected as a volatile flavor component of roasted filberts(1), baked potatoes(2), blue cheese(3), Beaufort (Gruyere) cheese(4), fried bacon(5), clove essential oil(6), chickpeas(7), fried chicken(8), earth almonds (Cyperus esculentus L.)(14), frankfurters(15), raw beef(17), and in food products processed from the Cassava root(9). 2-Heptanone has been identified in swiss cheese (0.45 ppm) evaporated milk, butter, milk, cream (0.004-0.007 ppm), milk fat (16 ppm), white bread, soybeans (1 ppm) peaches and orange juice(10). 2-Heptanone has been measured in canned cream corn (6 ppb), canned corn (21 ppb), frozen corn (3 ppb) and fresh corn (18 ppb)(11). 2-Heptanone was found in popcorn using wet extraction method at 60 ug/kg and dry extraction method at 17 ug/kg(12). Commercial rice cakes were found to contain 15 ppb of 2-heptanone(13). Fermented soybean (Glycine max) curds were found to contain 601.7 to 972.6 ug/kg of 2-heptanone(16). 2-Heptanone was found in uncured beef (0.21 mg/kg), chicken (0.54 mg/kg) and pork (0.20 mg/kg)(18). 2-Heptanone was detected in whole and ground musty sorghum with direct helium-purge method and with supercritical fluid extraction method(19). 2-Heptanone was isolated as a volatile component of duck meat (5.68 ppb), duck fat (11.62 ppb), Cantonese style roasted duck (38.44 ppb) and Cantonese style roasted duck gravy (63.45 ppb)(20). 2-Heptanone was measured at 146 ng/g, 455 ng/g, 115 ng/g and 42 ng/g in anchovy paste, big eyed herring paste, hair tail viscera paste and shrimp paste, respectively(21).
Exposure Routes
The substance can be absorbed into the body by inhalation of its vapour.
inhalation, ingestion, skin and/or eye contact
Toxicity Summary
The existing information was reviewed by the independent Expert Panel for Fragrance Safety and supports the use of 2-Heptanone as described in this fragrance ingredient safety assessment. Data show that it is not genotoxic and provide a calculated Margin of Exposure (MOE) greater than 100 for the repeated dose toxicity and reproductive toxicity endpoints. Data show that there are no safety concerns for skin sensitization under the current declared levels of use. 2-Heptanone is not expected to be photoirritating/photoallergenic based on evaluation of the ultraviolet/visible (UV/Vis) spectra. The local respiratory toxicity endpoint was evaluated using the read-across analog 4-methyl-2-pentanone, with a calculated MOE greater than 100.
Signs and Symptoms
Cough. Dizziness. Headache. Unconsciousness. Blurred vision.
Dry skin. Redness.
Redness.
irritation eyes, skin, mucous membrane; headache; narcosis, coma; dermatitis
Regulatorische Informationen
FDA Requirements
2-Heptanone is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient. Synthetic flavoring substances and adjuvants /incl 2-Heptanone/ may be safely used in foods.
FIFRA Requirements
Residues of 2-heptanone are exempted from the requirement of a tolerance when used as a solvent, co-solvent in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest.
Residues of 2-heptanone are exempted from the requirement of a tolerance when used as a solvent, co-solvent in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals.
Sicherheitsdaten
- OEB
- A
- OEL
- TWA: 100 ppm (465 mg/m3)
- wgk
- 2
- IDLA
- 800 ppm
- tsca
- TSCA listed
- ridadr
- UN 1110
- hs_code
- 29141990
- RTECS-Nr.
- MJ5250000
- risk_code
- 22-38-40-48/20/22-20/22-10
- Toxizität
- LD50 orally in Rabbit: 1670 mg/kg LD50 dermal Rabbit 10332 mg/kg
- hazard_code
- Xn
- safety_code
- 36-24/25
- hazard_class
- 3
- packing_group
- III
- Speicherklasse
- 3 - Flammable liquids
- Giftige Stoffe Daten
- 110-43-0(Hazardous Substances Data)
- Hazard Classifications
- Acute Tox. 4 InhalationAcute Tox. 4 OralFlam. Liq. 3STOT SE 3
- Selbstentzündungstemperatur
- 739 °F
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
MnAK undergoes carbonyl reduction to a secondary alcohol and omega-1 oxidation to a hydroxyketone, which is further oxidized to 2,6-heptanedione.
When 950 mg methyl amyl ketone/kg body weight was administered orally to rabbits, 40% was excreted as heptyl-2-glucuronide, and traces of the unchanged ketone were also found in the urine. 2-Heptanone ... was identified ... among ... 300 compounds present in the volatile constituents of urine from male and female subjects.
A subchronic inhalation study was conducted in which male rats and monkeys were exposed to 0, 131, or 1025 ppm methyl n-amyl ketone for 10 mo (6 hr/day, 5 days/wk). Methyl n-amyl ketone and methyl n-amyl alcohol were detected in the urine and serum of monkeys exposed to methyl n-amyl ketone.
/It was/ reported that 41% of an orally administered dose of 0.95g/kg /methyl n-amyl ketone/ in rabbits was excreted as 2-heptyl glucuronide ...Inhibition of P450 2EL increases the amount of MnAK exhaled.
Absorption, Distribution and Excretion
Results of tissue distribution studies of (14)C methyl n-amyl ketone in rats comparing ip and inhalation routes of exposure were similar. Liver tissue had the highest level of radioactivity regardless of the route of admin; however, no liver pathology was observed. Urinary excretion accounted for 25% of the admin dose after 12 hr.
/It was/ reported that 41% of an orally administered dose of 0.95g/kg /methyl n-amyl ketone/ in rabbits was excreted as 2-heptyl glucuronide ...Inhibition of P450 2EL increases the amount of MnAK exhaled.
Verwendung und Herstellung
Uses
Used as a solvent for resins and lacquers, a fragrance for cosmetics, and a flavor for foods; [HSDB]
Painting (Solvents) [Category: Paint]
Industrial solvent; solvent for synthetic resin finishes; fragrance ingredient in creams, lotions, perfumes, soaps & detergents; flavor ingredient in foods; inert reaction medium
Solvent for nitrocellulose lacquers.
Blue cheese flavor
In perfumery as constituent of artificial carnation oils; as industrial solvent
U.S. Production
2023: 100,000,000 - <250,000,000 lb
This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
(1972) GREATER THAN 4.54X10+5 G
(1975) GREATER THAN 4.54X10+5 G
(1986) >10 million-50 million pounds
For more U.S. Production (Complete) data for 2-HEPTANONE (8 total), please visit the HSDB record page.
Methods of Manufacturing
Produced industrially by reductive condensation of acetone with butyraldehyde in one or two steps.
Prepd by the ketone decomposition of ethyl butylacetoacetate; by hydration of 1-heptyne and 2-heptyne
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
Furniture and Related Product Manufacturing
2-Heptanone: ACTIVE
Reported uses: in non-alcoholic beverages at 2.7 ppm; ice cream, ices, etc 6.0 ppm; candy 6.4 ppm; baked goods 13 ppm; & condiments 10-25 ppm.
Anwendungen
Beschreibung2-Heptanone has a characteristic banana, slightly spicy odor. It may be prepared by oxidation of methyl n-amyl carbinol; also from n-amyl propionic acid or from ethyl butyl acetat.
OccurrenceReported found in clove essential oil, Ceylon cinnamon and rancid coconut oil; also identifed in Ruta Montana Also reported found in banana, lingonberry, loganberry, black currant, guava, grapes, papaya, peach, pear, raspberry, other berries, strawberry jam, asparagus, roasted onion, leek, baked potato, mushroom, clove bud, ginger, blue, cheddar and Swiss cheeses, milk, cream, butter, fsh, meats, hop oil, beer, brandy, rum, malt whiskey, grape wines, cocoa, coffee, tea, peanuts, pecans, walnut, oats, soybeans, coconut oil, olive, passion fruit, mango, fgs, rice, sweet corn, corn tortillas, malt, caviar, shrimp, oysters, crab, crayfsh and mate
Verwenden2-Heptanone is used as an industrial solvent; a solvent for synthetic resin finishes; an inert reaction medium; a flavor ingredient in foods; a fragrance ingredient in creams, lotions, perfumes, soaps, and detergents.
Darstellung
synthetischeBy oxidation of methyl n-amyl carbinol; also from n-amyl propionic acid or from ethyl butyl acetate.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: Heptan-2-one is a dialkyl ketone with methyl and pentyl as the alkyl groups. It has a role as a pheromone and a mouse metabolite. It is a dialkyl ketone and a methyl ketone.
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