DL-Mevalonolactone ((±) -Mevalonolactone; Mevalolactone) is the δ-lactone form of mevalonic acid, a precursor for cholesterol and isoprenoid synthesis, with oral activity against HMGCR mutations and statin-induced myopathy. DL-Mevalonolactone induces inflammation and oxidative stress responses, reducing mitochondrial membrane potential and leading to mitochondrial swelling." />

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Chemical Structure| 674-26-0 Chemical Structure| 674-26-0
Chemical Structure| 674-26-0

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CAS No.: 674-26-0

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DL-Mevalonolactone ((±) -Mevalonolactone; Mevalolactone) is the δ-lactone form of mevalonic acid, a precursor for cholesterol and isoprenoid synthesis, with oral activity against HMGCR mutations and statin-induced myopathy. DL-Mevalonolactone induces inflammation and oxidative stress responses, reducing mitochondrial membrane potential and leading to mitochondrial swelling.

Synonyms: (±)-Mevalonolactone; Mevalolactone; NSC 90804

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Product Details of DL-Mevalonolactone

CAS No. :674-26-0
Formula : C6H10O3
M.W : 130.14
SMILES Code : CC1(O)CCOC(=O)C1
Synonyms :
(±)-Mevalonolactone; Mevalolactone; NSC 90804
MDL No. :MFCD00006648

Safety of DL-Mevalonolactone

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of DL-Mevalonolactone

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 674-26-0 ]

[ 674-26-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 674-26-0 ]
  • [ 3944-36-3 ]
  • [ 611-14-3 ]
  • [ 106-42-3 ]
  • [ 526-73-8 ]
  • [ 64-19-7 ]
  • [ 802294-64-0 ]
  • [ 108-38-3 ]
  • [ 67-64-1 ]
  • [ 108-88-3 ]
  • [ 78-93-3 ]
YieldReaction ConditionsOperation in experiment
With ZSM-5; In water; at 200℃; under 27002.7 Torr;Flow reactor; Molecular sieve; Catalytic Results with ZSM-5 (0104) As in the case of amorphous SiO2/Al2O3, unconverted mevalonolactone was not detected in the liquid product of any of the investigated temperatures with ZSM-5 catalysis. This indicated that full conversion of mevalonolactone was also achieved under the conditions studied with ZSM-5. The composition of the liquid products by GC-MS and the gaseous products as a function of temperature over ZSM-5 is presented in Tables 4 and 5 respectively. (0105) At 200 C., the liquid product of the reaction was an emulsion-like homogeneous solution. The main products obtained are the anhydrous form of mevalonolactone and 3-methyl-2-butanone. Limited amounts of CO2 were detected in the gas products. Compared to the amorphous silica-alumina, where only dehydrated mevalonolactone was observed at 200 C., the much more acidic ZSM-5 catalyst not only catalyzed dehydration, but also decarboxylation. (0106) At 400 C., the liquid product separated into two distinct phases: an oily phase, forming a top layer, and an aqueous emulsion-like phase. The two phases were again separated and analyzed separately. The aqueous phase consisted mainly of acetic/propanoic acid, acetone, and toluene. In contrast to 200 C. and the results with amorphous silica alumina, no 3-methyl-2-butanone was observed. This indicates the occurrence of extensive decarboxylation/cracking reactions. The oily phase was comprised of aromatic compounds, such as p-xylene, toluene, 1,2,3-trimethyl-benzene, and 1-ethyl-2-methyl-benzene. These aromatics are probably a result of oligomerization reactions of olefins which form as intermediates over ZSM-5. CO2 and small amounts of light hydrocarbons (alkanes/alkenes) were detected in the gas phase, as shown in Table 5. [table-us-00004-en] TABLE 4 Analysis of liquid products by GC-MS obtained over ZSM-5 Conditions 4 5 WHSV, h-1 1 1 Pressure, bar 36 36 Temperature, C. 200 400 GC-MS analysis, area % Lower Upper Mevalonolactone Dehydromevalonic lactone 66.15 No matches found 0.31 6.04 Ethyl alcohol 0.28 3.10 Butane 0.55 2-Propanol, 2-methyl- 3.28 Propanal, 2,2-dimethyl- 0.56 2-Butanone 0.32 Butanal, 2,2-dimethyl- 0.3 2-Butanone, 3-methyl- 15.75 Acetone 23.10 2-Butanone 5.44 Acetic acid 0.35 40.50 Propanoic acid 5.07 Isopropyl Alcohol 4.62 2-Propanol, 1-(1-methylethoxy)- 5.10 p-Xylene 3.79 22.7 o-xylene 1.11 Benzene, 1,2,3-trimethyl- 13.34 Benzene, 1-ethyl-2-methyl- 1.96 12.58 Toluene 1.96 7.03 11.39 Benzene, 1,3-dimethyl- 6.92 Benzene, 4-ethyl-1,2-dimethyl- 3.45 2-Tolyloxirane 1.42 Benzene, 1,3,5-trimethyl- 2.59 Benzene, 1-methyl-2-(1- 0.73 methylethyl Benzene, 1-methyl-3-propyl- 1.21 Naphthalene, 1-methyl- 1.16 Naphthalene, 2,7-dimethyl- 1.07 1-Phenyl-1-butene 1 Benzene, (1-methyl-1-buteny1)- 0.89 Benzene, 1-methyl-4-(1- 0.86 methylethyl Benzene, 1,3-diethyl- 0.86 Benzene, 2-butenyl- 0.69 Benzene, propyl- 0.6 Naphthalene, 1,2,3,4-tetrahydro-6- 1.54 methyl- Other* 19.32 TOTAL 100 100 100 [table-us-00005-en] TABLE 5 Analysis of gaseous products obtained over ZSM-5 Conditions 4 5 WHSV, h-1 1 1 Pressure, bar 36 36 Temperature, C. 200 400 GC analysis, vol % Hydrogen 0.06 Methane Ethane Ethylene Propane 0.46 Propylene 0.06 Isobutane 0.02 0.68 n-butane 0.14 1-butene Isobutylene 1.15 0.05 Trans-2-butene 0.02 Cis-2-butene 1,3-butadiene Isopentane 0.22 n-pentane 1-pentylene C5+/C6+ 0.55 0.34 CO2 8.58 4.65 (??) CO 0.47 N2 93.26 90.20 Total 103.55 97.35
 

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