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303143

3,6-Dimethyl-1,4-dioxane-2,5-dione

99%

Synonym(s):

DL-Lactide, rac-Lactide, Lactide

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$92.10

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$280.00

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About This Item

Empirical Formula (Hill Notation):
C6H8O4
CAS Number:
95-96-5
Molecular Weight:
144.13
EC Number:
202-468-3
MDL number:
MFCD00011685
UNSPSC Code:
12352100
PubChem Substance ID:
24858300
NACRES:
NA.22

Key Documents

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Quality Level

200

assay

99%

form

crystals

bp

142 °C/8 mmHg (lit.)

mp

116-119 °C

functional group

ester

storage temp.

2-8°C

SMILES string

CC1OC(=O)C(C)OC1=O

InChI

1S/C6H8O4/c1-3-5(7)10-4(2)6(8)9-3/h3-4H,1-2H3

InChI key

JJTUDXZGHPGLLC-UHFFFAOYSA-N

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1 of 4

This Item
367044851450765112
3,6-Dimethyl-1,4-dioxane-2,5-dione 99%

Sigma-Aldrich

303143

3,6-Dimethyl-1,4-dioxane-2,5-dione

(3S)-cis-3,6-Dimethyl-1,4-dioxane-2,5-dione 98%

Sigma-Aldrich

367044

(3S)-cis-3,6-Dimethyl-1,4-dioxane-2,5-dione

D-(+)-Glucuronic acid γ-lactone ≥99%

Sigma-Aldrich

851450

D-(+)-Glucuronic acid γ-lactone

Poly(L-lactide) average Mn 10,000, PDI ≤1.1

Sigma-Aldrich

765112

Poly(L-lactide)

assay

99%

assay

98%

assay

≥99%

assay

-

Quality Level

200

Quality Level

100

Quality Level

200

Quality Level

100

mp

116-119 °C

mp

92-94 °C (lit.)

mp

172-175 °C (lit.)

mp

-

bp

142 °C/8 mmHg (lit.)

bp

-

bp

-

bp

-

form

crystals

form

crystals

form

powder

form

solid

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

General description

3,6-Dimethyl-1,4-dioxane-2,5-dione (or rac-lactide), is the 50:50 racemic mixture of D- and L-Lactide. Rac-lactide is a lactone derived from lactic acid that has attracted great interest in academia and commercial applications, as it is derived from abundant renewable resources. Rac-lactide can be ready polymerized via ring-opening polymerization, using a variety of metal or organocatalysts, yielding poly(D,L-lactide). While the resulting polymer is generally amorphous, the use of stereospecific catalysts can lead to heterotactic PLA, which exhibits some degree of crystallinity.

Application

3,6-Dimethyl-1,4-dioxane-2,5-dione can be used as a reactant:
  • To synthesize multi-block copolymers of polylactide and polycarbonate.
  • In the aluminum-catalyzed polymerization of propene oxide, lactide, and phthalic anhydride to produce multi-block polyesters.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCN5045
BCCL8455
BCCM5564
BCCL9376
BCCL7050

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Tetrahedron Letters, 47, 6517-6517 (2006)
Vibrational Optical Activity of (3 S, 6 S)-3, 6-Dimethyl-1, 4-dioxane-2, 5-dione.
Tam CN, et al.
Journal of the American Chemical Society, 118(42), 10285-10293 (1996)
Lu Qin et al.
Dalton transactions (Cambridge, England : 2003), 48(32), 12315-12325 (2019-07-26)
In this paper we report a series of Al(iii) complexes supported by N,O-bidentate β-pyrazyl functionalized enolate ligands HL1-HL5 (L = (6-Me-2,5-C4H2N2)-CH[double bond, length as m-dash]C(R)-O-), (R = tBu, Ph, p-tolyl, p-OMePh, o-tolyl) and their exploitation for the ring-opening polymerization of
Hendrik Vögeling et al.
Materials science & engineering. C, Materials for biological applications, 103, 109749-109749 (2019-07-28)
Catheter related infections are causing one third of all blood stream infections. The mortality of those infections is very high and the gold standard for catheter related blood stream infections (CR-BSI) is still the removal of the catheter and systemic
Yutong Han et al.
Advanced science (Weinheim, Baden-Wurttemberg, Germany), 6(15), 1900251-1900251 (2019-08-14)
Due to specific immune recognition receptors on the surface of T cells, their membranes are promising mimic nanocarriers for delivering drugs to tumor lesions. However, this single targeting strategy potentially compromises therapy efficacy for tumor targeting due to inter- and
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Questions

1–3 of 3 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

      Helpful?

  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

      Helpful?

  3. I have purchased the lactide, and its a mixture of L and D right? also, if I want to purchase L-lactide how much is it? because I couldn't find it.

    1 answer

    1. This product, 3,6-Dimethyl-1,4-dioxane-2,5-dione (or rac-lactide), is the 50:50 racemic mixture of D- and L-Lactide.

      L-lactide is available on the website under the product number "36704".
      For more information, please visit https://www.sigmaaldrich.com/US/en/product/aldrich/367044

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