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674-26-0

Basic Information
CAS No.: 674-26-0
Name: DL-Mevalonolactone
Article Data: 42
Molecular Structure:
Molecular Structure of 674-26-0 (DL-Mevalonolactone)
Formula: C6H10 O3
Molecular Weight: 130.144
Synonyms: 2H-Pyran-2-one,tetrahydro-4-hydroxy-4-methyl-, (?à)- (8CI); (RS)-Mevalonolactone; (?à)-Mevalolactone; (?à)-Mevalonolactone; DL-Mevalonic acid lactone;DL-Mevalonic acid d-lactone; DL-Mevalonolactone; MVSL; Mevalolactone; Mevalonic acid lactone;Mevalonic acid d-lactone;Mevalonic lactone; Mevalonolactone; NSC 90804; b-Hydroxy-b-methyl-d-valerolactone
EINECS: 211-615-0
Density: 1.189 g/cm3
Melting Point: 28 °C(lit.)
Boiling Point: 145-150 °C5 mm Hg(lit.)
Flash Point: >230 °F
Solubility: Soluble in ethanol (100 mg/ml-clear to very slightly hazy faint yellow solution), dichloromethane, ethyl acetate, and methanol
Appearance: Moist pale yellow to off white solid
PSA: 46.53000
LogP: 0.07440
Synthetic route
7564-64-9

3-methyl-1,3,5-pentanetriol

674-26-0

mevalonolactone

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane for 4h; Ambient temperature;92%
With aluminum oxide; sodium bromite In dichloromethane for 1.5h; Ambient temperature;85%
With peracetic acid; sodium bromide In ethyl acetate at 39.9℃; for 2h;83%
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate In acetonitrile at 22℃; for 6h;83%
118617-84-8

4-(4-Methoxy-benzyloxymethoxy)-4-methyl-tetrahydro-pyran-2-one

674-26-0

mevalonolactone

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water for 10h; Ambient temperature; cleavage of (p-methoxybenzyloxy)methyl protecting group;89%
99720-12-4

2,3,5,6-tetrahydro-4-methylpyran-2,4-diol

674-26-0

mevalonolactone

Conditions
ConditionsYield
With sodium acetate; pyridinium chlorochromate In dichloromethane for 6h; Ambient temperature;82%
Conditions
ConditionsYield
With sulfuric acid for 15h; Reflux;82%
Multi-step reaction with 2 steps
1: tetrabutylammomium bromide / tetrahydrofuran / 4 h / 50 °C / Inert atmosphere
2: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
View Scheme
2754-27-0

trimethylsilyl acetate

81852-67-7

4-((trimethylsilyl)oxy)-3-butanone

674-26-0

mevalonolactone

Conditions
ConditionsYield
With lithium diisopropyl amide 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 2 h;81%
80514-97-2

ethyl 3-hydroxy-3-methyl-5-<(2-tetrahydropyranyl)-oxy>pentanoate

674-26-0

mevalonolactone

Conditions
ConditionsYield
With acetyl chloride In ethanol for 10h; Ambient temperature;80%
With acetyl chloride In ethanol Ambient temperature; overnight;22 g
34695-32-4

3-hydroxy-3-methylglutaric anhydride

674-26-0

mevalonolactone

Conditions
ConditionsYield
With sodium tetrahydroborate In isopropyl alcohol75.6%
With sodium tetrahydroborate In isopropyl alcohol Ambient temperature;300 mg
With sodium tetrahydroborate In isopropyl alcohol for 24h; Ambient temperature;
Multi-step reaction with 2 steps
1: 1.) CH2Cl2, -20 deg C, 7 days
2: 1.) LiCl, NaBH4; 2.) 10percent KOH / 1.) EtOH, 50 deg C, 24 h; 2.) MeOH, 60 deg C, 4h
View Scheme
32315-10-9

bis(trichloromethyl) carbonate

1452161-92-0

benzyl 3,5-dihydroxy-3-methylpentanoate

A

1452161-93-1

benzyl 2-(4-methyl-2-oxo-1,3-dioxan-4-yl)acetate

B

674-26-0

mevalonolactone

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;A 64%
B 12%
128811-87-0

5-chloro-3-hydroxy-3-methylvaleric acid

674-26-0

mevalonolactone

Conditions
ConditionsYield
With potassium carbonate; Katamin AB In acetone at 40 - 45℃; for 3h;60%
246237-03-6

5-[(4-nitrophenyl)methylcarbamoyloxy]-3-hydroxy-3-methylpentanoic acid

674-26-0

mevalonolactone

Conditions
ConditionsYield
With sodium hydroxide In methanol at 20℃; Cyclization; Deprotection;17%
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    674-26-0

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Chemistry

Product Name: DL-Mevalonolactone (CAS NO.674-26-0)

Molecular Formula: C6H10O3
Molecular Weight: 130.14g/mol
Mol File: 674-26-0.mol
EINECS: 211-615-0
Melting Point: 28 °C(lit.)
Boiling point: 274.9 °C at 760 mmHg
Storage Temperature: 2-8°C
Flash Point: 126.8 °C
Density: 1.189 g/cm3
Refractive index: n20/D 1.473(lit.)
Index of Refraction: 1.478  Molar Refractivity: 30.99 cm3 
Molar Volume: 109.4 cm3 
Surface Tension: 42.5 dyne/cm
Enthalpy of Vaporization: 59.6 kJ/mol
Vapour Pressure: 0.000662 mmHg at 25°C
XLogP3-AA: -0.3
H-Bond Donor: 1
H-Bond Acceptor: 3
Structure Descriptors of DL-Mevalonolactone (CAS NO.674-26-0):
  IUPAC Name: 4-hydroxy-4-methyloxan-2-one
  Canonical SMILES: CC1(CCOC(=O)C1)O
  InChI: InChI=1S/C6H10O3/c1-6(8)2-3-9-5(7)4-6/h8H,2-4H2,1H3 
  InChIKey: JYVXNLLUYHCIIH-UHFFFAOYSA-N
Product Categories: Pale Yellow OilHeterocycles; Metabolites & Impurities

Safety Profile

Safety Information of DL-Mevalonolactone (CAS NO.674-26-0):
WGK Germany: 3
F: 3-10

Specification

 DL-Mevalonolactone , its CAS NO. is 674-26-0, the synonyms are DL-Mevalonic acid lactone ; (4R)-4-Hydroxy-4-methyl-oxan-2-one ; (+/-)-Tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-one .