Lactide

HCID 7272

Basic information

CAS
33135-50-1
Standard SMILES
CC1OC(=O)C(C)OC1=O
InChIKey
JJTUDXZGHPGLLC-UHFFFAOYSA-N
Molecular formula
C6H8O4
Average molar mass
144.12 g/mol
Monoisotopic mass
144.04225874

Overview

Lactide is a member of dioxanes.

Names & identifiers

Preferred name
Lactide
IUPAC
3,6-dimethyl-1,4-dioxane-2,5-dione
English name
DL-Lactide
Molecular formula
C6H8O4
Molecular weight
144.13

Names & synonyms

95-96-5LACTIDEDilactidep-Dioxane-2,5-dione, 3,6-dimethyl-RefChem:57699202-468-33,6-Dimethyl-1,4-dioxane-2,5-dioneDL-Lactide33135-50-1DL-Dilactide1,4-Dioxane-2,5-dione, 3,6-dimethyl-3,6-Dimethyl-2,5-dioxo-1,4-dioxane
Show more names
LACTIC ANHYDRIDE2-hydroxy-propanoicacibimol.cyclicesterD,L-Lactide S5-Dione,3purasorbl
Lactic acid, bimol. cyclic ester7EH08MWO6MMFCD00011685Propanoic acid, 2-hydroxy-, bimol. cyclic esterDTXSID7041253AI3-05059LACTIDE, DL-NSC-403080

Database identifiers

CAS
33135-50-1、95-96-5
PubChem CID
7272
DTXSID
DTXSID7041253
ChEMBL
CHEMBL3185272
ChEBI
CHEBI:177651
UNII
7EH08MWO6M
EC Number
202-468-3、608-832-1
Nikkaji
J4.715E

Properties

Computed structural properties

XLogP
0.6
Topological polar surface area
52.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
0
Heavy atoms
10

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Other Organic Compounds
Physical Description · 2 items

CBI

Solid; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
116 · 116-119 °C
Boiling point
142 °C8 · 142 °C8 mm Hg(lit.)
Density
1.186 · 1.186±0.06 g/cm3(Predicted)
vapor pressure
0.311 Pa · 0.311Pa at 25℃
Flash point
180 °C · 180°C
storage temp.
2 · 2-8°C

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 158 reports by companies from 6 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 2 items

1,4-Dioxane-2,5-dione, 3,6-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Dioxane-2,5-dione, 3,6-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 13-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15774

Hazards SummaryCauses stomach ulceration and changes in renal tubules in 2-week intermittent oral studies of dogs; [RTECS] A skin and strong eye irritant; [Sigma-Aldrich MSDS] See 4,4-Dimethyl-1,3-dioxane and 1,4-Dioxane.
Hazard Classes and CategoriesEye Irrit. 2A (100%)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
2
tsca
TSCA listed
rtecs
JH1100000
hs_code
29322090
risk_code
36/37/38-36

Chemistry & industry

Uses & manufacturing

UsesUsed to make polylactic acid and cosmetics; [ExPub: ECHA REACH Registrations]
U.S. Production2023: 100,000,000 - <500,000,000 lb
Consumer UsesIntermediate
Industry UsesIntermediate
General Manufacturing Information · 2 items

Plastics Product Manufacturing

1,4-Dioxane-2,5-dione, 3,6-dimethyl-: ACTIVE

Applications · 4 items

UsesDL-Lactide is used to produce 2-hydroxy-propionic acid 1-(1-phenyl-ethoxycarbonyl)-ethyl ester. It acts as an important raw material and an intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyes. It is involved in enzymatic alcoholysis to produce both alkyl (R)-lactates and alkyl (S,S)-lactyllactates.DL-Lactide is often used as a protective layer in wound coatings, or as anchors, screws or mesh in surgery, since it degrades in about six months to the innocuous lactic acid.

UsesDL-Lactide is used to produce 2-hydroxy-propionic acid 1-(1-phenyl-ethoxycarbonyl)-ethyl ester. It acts as an important raw material and an intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyes. It is involved in enzymatic alcoholysis to produce both alkyl (R)-lactates and alkyl (S,S)-lactyllactates.

UsesEnzymatic alcoholysis of this racemic lactide catalyzed by commercial Novozym® 435 produces both alkyl (R)-lactates and alkyl (S,S)-lactyllactates in good yield and high enantiopurity.

General Description3,6-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.

Upstream & downstream products

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
上海康朗生物科技有限公司021-61998208 18217752821 · [email protected]
苏州启航生物科技有限公司18151111370 · [email protected]

Additional notes

DefinitionChEBI: Lactide is a member of dioxanes.

Related reactions

5 records

Compound notes

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