3-Hydroxy-2-methyl-4H-pyran-4-one

Iupac Name：3-hydroxy-2-methylpyran-4-one

Molecular Weight：126.111

Modify Date.: 2022-10-27 13:10

Introduction: 3-hydroxy-2-methyl-4h-pyran-4-one (also named as Maltol, Larixinic acid, Palatone and Veltol) is a natural compound. Maltol is found in chicory, roasted malt, breads, milk, heated butter, uncured smoked pork, cocoa, coffee, roasted barley, roasted peanuts, roasted filbert, soybean, in the bark of larch tree, in pine needles, and in roasted malt (from which it gets its name) etc. It has the odor of cotton candy and caramel. Maltol is widely used as flavor enhancer to improve mouthfeel and to enhance flavor of candy and baked foods in food production and of soft drinks in beverage industry. It is used as intermediate in pharmaceutical for medicine manufacturing. It is used as flavoring agent in cosmetic and personal care industries to enhance flavor. According to FEEDAP Panel, maltol is safe to be added to feed for all animal species at the normal use level of 5 mg/kg feed. View more+

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1. Names and Identifiers

1.1 Name: 3-Hydroxy-2-methyl-4H-pyran-4-one
1.2 Synonyms: 2-methyl-3-hydroxy-4H-pyran-4-one 2-methyl-3-hydroxy-4-pyranone 2-methyl-3-oxy-4H-pyran-4-one 3-hydroxy-2-methyl-4-pyrone 3-Hydroxy-2-methyl-4-pyrone,Maltol 3-Hydroxy-2-methyl-g-pyrone 4H-Pyran-4-one, 3-hydroxy-2-methyl- EINECS 204-271-8 FEMA 2656 Laricin MALTENE Maltol MALTOL FCC MFCD00006578 Palatone Talmon Veltol Vetol

1.3 CAS No.: 118-71-8

1.4 CID: 8369

1.5 EINECS(EC#): 204-271-8

1.6 Molecular Formula: C6H6O3 (isomer)

1.7 Inchi: InChI=1S/C6H6O3/c1-4-6(8)5(7)2-3-9-4/h2-3,8H,1H3

1.8 InChkey: XPCTZQVDEJYUGT-UHFFFAOYSA-N

1.9 Canonical Smiles: CC1=C(C(=O)C=CO1)O

1.10 Isomers Smiles: CC1=C(C(=O)C=CO1)O

2. Properties

2.1 Density: 1.348

2.1 Melting point: 160-164℃

2.1 Boiling point: 324 to 327° F (NTP, 1992)

2.1 Refractive index: n20/D 1.541

2.1 Flash Point: 127.3°C

2.1 Precise Quality: 126.03200

2.1 PSA: 50.44000

2.1 logP: 0.65380

2.1 Solubility: methanol: 50?mg/mL, clear

2.2 Appearance: White crystalline powder

2.3 Storage: Maltol solutions may be stored in glass or plastic containers. Thebulk material should be stored in a well-closed container, protectedfrom light, in a cool, dry place.

2.4 Color/Form: Powder

2.5 Decomposition: When heated to decomposition it emits acrid smoke and irritating fumes.

2.6 Odor: Fragrant, caramel-like odor

2.7 PH: pH of 0.5% aqueous solution = 5.3

2.8 Physical: PHYSICAL DESCRIPTION: White crystalline powder with a fragrant caramel-butterscotch odor. pH (5% aqueous solution) 5.3. (NTP, 1992)

2.9 pKa: 8.41±0.10(Predicted)

2.10 Water Solubility: 1.2 g/100 mL (25 oC)

2.11 Stability: Stable.

2.12 StorageTemp: Store in a cool, dry place. Store in a tightly closed container.

2.13 Toxicity Summary: IDENTIFICATION AND USE: Maltol; is a white crystalline powder. It is used as a flavoring agent, to impart "freshly baked" odor and flavor to breads and cakes. It is also used as medication. HUMAN EXPOSURE AND TOXICITY: Maltol; at concentrations ranging from 0.1 to 1.5 umol/mL induced sister chromatid exchanges in human lymphocytes. It was suggested that these results were due to an indirect action of maltol; and not to its direct reactivity with DNA. ANIMAL STUDIES: Eight female mice were fed a diet containing maltol; at a level of 0.5% (w/w) for 21 weeks, calculated to provide an average daily intake of 750 mg/kg bw. At termination, no differences in general health, behavior, body-weight gain or relative liver weights were reported. Gross and microscopic examination revealed no histological abnormalities in the livers of the treated mice when compared with the controls. A three-generation study of reproductive toxicity was conducted, in which groups of 20 male and 20 female rats were given diets containing maltol; at concentrations resulting in 100, 200 or 400 mg/kg bw per day. On day 134, animals of the F1 generation showed signs of sialodacryodenitis due to a contagious virus. No deaths occurred, and the signs diminished within 10 days. Maltol; had no effect on copulation rate, mating viability index, lactation, offspring sex ratio or 21-day pup survival index. Maltol; at concentrations ranging from 0.1 to 1.5 umol/mL induced sister chromatid exchanges in Chinese hamster ovary cells. It was suggested that these results were due to an indirect action of maltol; and not to its direct reactivity with DNA. Maltol; was weakly mutagenic (two- to threefold increases in number of revertants) in Salmonella typhimurium TA100 at concentrations of 1-3 mg/plate either alone or with metabolic activation. Activity against TA98 was not detected. Maltol; tested at concentrations of 0.1-10.0 mg/plate increased the number of revertants in strain TA97 at 1 mg/plate by about twofold. No increase found in the presence of an activation system, or in TA102 alone or with activation. In other studies with S. typhimurium, maltol; was not consistently mutagenic when tested at concentrations up to 10,000 ug/plate alone or in the presence of an activation system.

3. Use and Manufacturing

3.1 Definition: ChEBI: A natural product found in Cordyceps sinensis.

3.2 General Description: White crystalline powder with a fragrant caramel-butterscotch odor. pH (5% aqueous solution) 5.3.

3.3 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 1164 companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 227 of 1164 companies. For more detailed information, please visit ECHA C&L website

Of the 15 notification(s) provided by 937 of 1164 companies with hazard statement code(s):

H302 (99.89%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (12.91%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (11.74%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (11.42%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501

3.4 Methods of Manufacturing: By alkaline hydrolysis of streptomycin; salts; also from piperdine; to pyromeconic acid; and subsequent methylation at the 2 position.

3.5 Produe Method: Maltol is mainly isolated from naturally occurring sources such asbeechwood and other wood tars; pine needles; chicory; and the barkof young larch trees. It may also be synthesized by the alkalinehydrolysis of streptomycin salts or by a number of other syntheticmethods.

3.6 Purification Methods: It crystallises from CHCl3, toluene, aqueous 50% EtOH or H2O, and is volatile in steam. It can be readily sublimed in a vacuum. It forms a Cu2+ complex. [Beilstein 17 III/IV 5916, 18/1 V 114.]

3.7 Usage: A fragrance molecule used in flavor enhancers and fragrances.

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: R22;R36/37/38

4.1 Safety Statements: S26;S37/39

4.1 Fire Hazard: Flash point data on 3-Hydroxy-2-methyl-4H-pyran-4-one are not available; however, 3-Hydroxy-2-methyl-4H-pyran-4-one is probably combustible.

4.2 Hazard Declaration: H302

4.2 RIDADR: 25kgs

4.2 Safety Profile: Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes. A skin irritant. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

4.3 Caution Statement: P301 + P312 + P330

4.3 Incompatibilities: Concentrated solutions in metal containers, including some gradesof stainless steel, may discolor on storage.

4.4 WGK Germany: 3

4.4 RTECS: UQ1050000

4.4 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UQ1050000

CHEMICAL NAME :: 4H-Pyran-4-one, 3-hydroxy-2-methyl-

CAS REGISTRY NUMBER :: 118-71-8

BEILSTEIN REFERENCE NO. :: 0112169

LAST UPDATED :: 199712

DATA ITEMS CITED :: 17

MOLECULAR FORMULA :: C6-H6-O3

MOLECULAR WEIGHT :: 126.12

WISWESSER LINE NOTATION :: T6O DVJ B1 CQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1410 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 550 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD16 - Lethal Dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 820 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 1620 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 1410 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 3720 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 90 gm/kg/90D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 20500 mg/kg/41D-I

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 250 mg/kg

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 26,487,1988 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X2610 No. of Facilities: 508 (estimated) No. of Industries: 3 No. of Occupations: 5 No. of Employees: 1733 (estimated) No. of Female Employees: 642 (estimated)

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : in CDCl3

13C NMR : Predict

1H NMR : 90 MHz in CDCl3

1H NMR : Predict

Predict 1H proton NMR

IR : KBr disc

Raman : 4880 A,200 M,powder

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

118-71-8Total: 12 Synthesis Route

9004-34-6 344 Suppliers

118-71-8 284 Suppliers

80-71-7 123 Suppliers

498-07-7 94 Suppliers

Literatures:
Environmental Science and Technology, , vol. 33, # 15 p. 2584 - 2592
Yield: null

60546-72-7

118-71-8 284 Suppliers

Literatures:
Otsuka Kagaku Yakuhin Kabushiki Kaishi Patent: US4059595 A1, 1977 ;
Yield: ~9%

63493-69-6

118-71-8 284 Suppliers

Literatures:
Weeks, Paul D.; Brennan, Thomas M.; Brannegan, Daniel P.; Kuhla, Donald E.; Elliot, Mark L.; et al. Journal of Organic Chemistry, 1980 , vol. 45, # 6 p. 1109 - 1113
Yield: ~74%

View all

8. Precursor and Product

precursor:

87251-66-9

553664-53-2

63493-69-6

9004-34-6

72690-06-3

66212-70-2

66187-06-2

67171-01-1

60546-72-7

95263-68-6

152547-41-6

product :

76015-11-7

72830-07-0

72830-08-1

87598-03-6

4780-14-7

30652-14-3

90037-22-2

65923-43-5

30652-24-5

107512-34-5

61049-69-2

117135-43-0

209248-75-9

61160-18-7

171253-88-6

919366-36-2

30652-11-0

17184-19-9

30652-12-1

72830-09-2

View all

9. Computational chemical data

Molecular Weight: 126.111g/mol
Molecular Formula: C₆H₆O₃
Compound Is Canonicalized: True
XLogP3-AA: 0.4
Exact Mass: 126.031694049
Monoisotopic Mass: 126.031694049
Complexity: 200
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 46.5
Heavy Atom Count: 9
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYBgMAAAAAAAAAAAAAAAAAAAAAAAAAAgAAAAAAAAAAAAAAAAGgAACAAACASggAICAAAABgCIAKBSAAIACAAgIAAICABAAEgAAAAAAAAAQAAAQAAIAYIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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CAS 118-71-8 Maltol C6H6O3 White powder