(+-)-Mevalonolactone

HCID 10428
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Basic information

CAS
674-26-0
Standard SMILES
CC1(O)CCOC(=O)C1
InChIKey
JYVXNLLUYHCIIH-UHFFFAOYSA-N
Molecular formula
C6H10O3
Average molar mass
130.14 g/mol
Monoisotopic mass
130.06299418

Names & identifiers

Preferred name
(+-)-Mevalonolactone
IUPAC
4-hydroxy-4-methyloxan-2-one
English name
DL-Mevalonolactone
Molecular formula
C6H10O3
Molecular weight
130.14

Names & synonyms

674-26-0DL-Mevalonic acid lactone1RJ06DC41B(+-)-MevalonolactoneRefChem:818792Mevalonolactone, (+-)-DL-Mevalonolactone4-Hydroxy-4-methyltetrahydro-2H-pyran-2-one4-hydroxy-4-methyloxan-2-oneD,L-Mevalonic Acid LactoneMevalolactone(+/-)-Mevalonolactone
Show more names
MEVALONOLACTONENSC 90804Beta-HydroHyperpure-MVADL-MEVALOLACTONE(±)-Mevalonolactone
MFCD000066484-hydroxy-4-methyl-tetrahydropyran-2-oneMevalonolactone, (+/-)-Mevalonic lactone503-48-0NSC-90804tetrahydro-4-hydroxy-4-Methylpyran-2-onebeta-Hydroxy-beta-methyl-delta-valerolactone

Database identifiers

CAS
674-26-0
PubChem CID
10428
DTXSID
DTXSID00964572
ChEMBL
CHEMBL4758470
ChEBI
CHEBI:95115
UNII
1RJ06DC41B
EC Number
211-615-0
Nikkaji
J38.600F

Properties

Computed structural properties

XLogP
-0.3
Topological polar surface area
46.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
9

Experimental & physicochemical properties

Collision Cross Section · 2 items

143.67 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

142.8 Ų [M+Na]+

Physicochemical properties

Melting point
28 °C · 28 °C(lit.)
Boiling point
145 · 145-150 °C5 mm Hg(lit.)
alpha
-1 · -1.0~+1.0°(20℃/D)(c=5, C2H5OH)
Density
1.1066 · 1.1066 (rough estimate)
refractive index
20 · n20/D 1.473(lit.)
Flash point
230 °F · >230 °F

Safety & regulation

GHS classification

GHS ClassificationNot Classified；Reported as not meeting GHS hazard criteria by 1 of 1 companies. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesNot Classified

Safety data

F
3-10
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
hs_code
29322090
Storage Class
11 - Combustible Solids

Chemistry & industry

Applications · 5 items

DescriptionDL-Mevalonolactone is the δ-lactone form of mevalonic acid, a precursor in the mevalonate pathway. It induces depolarization and swelling, decreases NADPH content and aconitase (ACO) activity, and increases malondialdehyde (MDA) production in calcium-loaded rat brain mitochondria. DL-Mevalonolactone reverses decreases in glucose uptake induced by simvastatin (Item Nos. 10010344 | 10010345) in L6 myotubes. Tissue levels and urinary excretion of DL-mevalonolactone are increased in patients with mevalonic aciduria, a disorder characterized by a deficiency in mevalonic kinase activity.

UsesA metabolite from endophytes of the medicinal plant Erythrina crista-galli.

UsesHMG CoA substrate

Uses(±)-Mevalonolactone is used to:study the effect of statin on the prenylation of Ras and Rho GTPasesanalyse the isoprenoid biosynthesis pathways in Listeria monocytogenesstudy the the effects of statins on proliferation and migration of HUVECs (HGF-induced human umbilical vein endothelial cells)

General DescriptionAlkaline hydrolysis of mevalonolactone gives mevalonate. Mevalonate is a precursor of farnesyl and geranylgeranyl pyrophosphates. These pyrophosphates are required for protein prenylation.

Upstream & downstream products

Downstream products

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
盐城通铭生物科技有限公司15195160625 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]

Additional notes

DefinitionChEBI: 4-hydroxy-4-methyl-2-oxanone is a delta-lactone.

Related reactions

4 records
New reaction record

Compound notes

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