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CAS No.: | 674-26-0 |
---|---|
Name: | DL-Mevalonolactone |
Article Data: | 42 |
Molecular Structure: | |
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 |
Conditions | Yield |
---|---|
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% |
4-(4-Methoxy-benzyloxymethoxy)-4-methyl-tetrahydro-pyran-2-one
mevalonolactone
Conditions | Yield |
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With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water for 10h; Ambient temperature; cleavage of (p-methoxybenzyloxy)methyl protecting group; | 89% |
2,3,5,6-tetrahydro-4-methylpyran-2,4-diol
mevalonolactone
Conditions | Yield |
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With sodium acetate; pyridinium chlorochromate In dichloromethane for 6h; Ambient temperature; | 82% |
D,L-mevalonic acid
mevalonolactone
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With lithium diisopropyl amide 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 2 h; | 81% |
ethyl 3-hydroxy-3-methyl-5-<(2-tetrahydropyranyl)-oxy>pentanoate
mevalonolactone
Conditions | Yield |
---|---|
With acetyl chloride In ethanol for 10h; Ambient temperature; | 80% |
With acetyl chloride In ethanol Ambient temperature; overnight; | 22 g |
3-hydroxy-3-methylglutaric anhydride
mevalonolactone
Conditions | Yield |
---|---|
With sodium tetrahydroborate In isopropyl alcohol | 75.6% |
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 |
bis(trichloromethyl) carbonate
benzyl 3,5-dihydroxy-3-methylpentanoate
A
benzyl 2-(4-methyl-2-oxo-1,3-dioxan-4-yl)acetate
B
mevalonolactone
Conditions | Yield |
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With pyridine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; | A 64% B 12% |
5-chloro-3-hydroxy-3-methylvaleric acid
mevalonolactone
Conditions | Yield |
---|---|
With potassium carbonate; Katamin AB In acetone at 40 - 45℃; for 3h; | 60% |
5-[(4-nitrophenyl)methylcarbamoyloxy]-3-hydroxy-3-methylpentanoic acid
mevalonolactone
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 20℃; Cyclization; Deprotection; | 17% |
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 Information of DL-Mevalonolactone (CAS NO.674-26-0):
WGK Germany: 3
F: 3-10
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 .