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MilliporeSigma

M4667

(±)-Mevalonolactone

~97% (titration)

Synonym(s):

(±)-β-Hydroxy-β-methyl-δ-valerolactone, (±)-3-Hydroxy-3-methyl δ-valerolactone, DL-Mevalolactone, DL-Mevalonic acid lactone

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1 G

$242.00

5 G

$778.00

10 G

$1,090.00

$242.00


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About This Item

Empirical Formula (Hill Notation):
C6H10O3
CAS Number:
Molecular Weight:
130.14
UNSPSC Code:
12352108
NACRES:
NA.25
PubChem Substance ID:
EC Number:
211-615-0
Beilstein/REAXYS Number:
80960
MDL number:
Assay:
~97% (titration)

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InChI key

JYVXNLLUYHCIIH-UHFFFAOYSA-N

InChI

1S/C6H10O3/c1-6(8)2-3-9-5(7)4-6/h8H,2-4H2,1H3

SMILES string

CC1(O)CCOC(=O)C1

assay

~97% (titration)

storage temp.

−20°C

Quality Level

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1 of 4

This Item
616699605980486604
assay

~97% (titration)

assay

≥97% (CP)

assay

99% (CP)

assay

98% (CP)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

storage temp.

−20°C

storage temp.

-

storage temp.

-

storage temp.

-

General description

Alkaline hydrolysis of mevalonolactone gives mevalonate.[1] Mevalonate is a precursor of farnesyl and geranylgeranyl pyrophosphates. These pyrophosphates are required for protein prenylation.[2]

Application

(±)-Mevalonolactone is used to:
  • study the effect of statin on the prenylation of Ras and Rho GTPases[2]
  • analyse the isoprenoid biosynthesis pathways in Listeria monocytogenes[3]
  • study the the effects of statins on proliferation and migration of HUVECs (HGF-induced human umbilical vein endothelial cells)[4]

Other Notes

May also be liquid!

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)


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Analysis of the isoprenoid biosynthesis pathways in Listeria monocytogenes reveals a role for the alternative 2-C-methyl-D-erythritol 4-phosphate pathway in murine infection.
Begley M
Infection and Immunity, 76, 5392-5401 (2008)
The effects of different types of statins on proliferation and migration of HGF-induced Human Umbilical Vein Endothelial Cells (HUVECs).
Burgazli KM
European Review for Medical and Pharmacological Sciences, 17, 2874-2883 (2013)
Coenzyme Q 10 production in recombinant Escherichia coli strains engineered with a heterologous decaprenyl diphosphate synthase gene and foreign mevalonate pathway.
Zahiri HS
Metabolic engineering, 8, 406-416 (2006)
Tomoyuki Nishimoto et al.
Toxicology and applied pharmacology, 223(1), 39-45 (2007-06-30)
High-dose statin treatment has been recommended as a primary strategy for aggressive reduction of LDL cholesterol levels and protection against coronary artery disease. The effectiveness of high-dose statins may be limited by their potential for myotoxic side effects. There is
Mareike Bongers et al.
eLife, 9 (2020-03-13)
Volatile isoprenoids produced by plants are emitted in vast quantities into the atmosphere, with substantial effects on global carbon cycling. Yet, the molecular mechanisms regulating the balance between volatile and non-volatile isoprenoid production remain unknown. Isoprenoids are synthesised via sequential

Articles

Cholesterol biosynthesis starts in the hepatic endoplasmic reticulum with acetyl-CoA, yielding 3-hydroxy-3-methylglutaryl-CoA via HMG-CoA synthase.

Questions

1–5 of 5 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. What chemical/s is this product soluble in for resuspension into a liquid form and at what concentration? I am wanting to add this to cell culture media.

    1 answer
    1. This product is soluble at a concentration of 0.5 g in 5 mL of 95% ethanol, equivalent to 100 mg/mL.

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  4. Why did M4667, (±)-Mevalonolactone, arrive as a liquid?

    1 answer
    1. As noted on the Sigma Aldrich web page for product M4667, (±)-Mevalonolactone, this product "may also be a liquid".  The melting point for this chemical is 26-28°C, which is approximately room temperature.  Because of this, the product may arrive as a liquid, but if stored at -20°C it should return to a solid/semi-solid state.  This product does not arrive in solution and will not have a concentration value.

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  5. What is the Department of Transportation shipping information for this product?

    1 answer
    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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