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
Show more names
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
- Formal charge
- 0
- Complexity
- 155
Experimental & physicochemical properties
Physical Description
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
- solubility
- Soluble in chloroform and methanol. Slightly soluble in benzene.
- form
- Crystalline Powder
- color
- White
- Water Solubility
- 16.3 g/L · 16.3g/L at 20℃
- Sensitive
- Moisture Sensitive
- BRN
- 82121 · 82121
- Cosmetics Ingredients Functions
- ABRASIVESKIN CONDITIONING
- InChI
- 1S/C6H8O4/c1-3-5(7)10-4(2)6(8)9-3/h3-4H,1-2H3
- InChIKey
- JJTUDXZGHPGLLC-UHFFFAOYSA-N
- SMILES
- CC1OC(=O)C(C)OC1=O
- LogP
- 0.4 at · 0.4 at 25℃
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 7 EH08MWO6M · 7EH08MWO6M
- NIST Chemistry Reference
- 1 · 1,4-Dioxane-2,5-dione, 3,6-dimethyl-(95-96-5)
- EPA Substance Registry System
- 1 · 1,4-Dioxane-2,5-dione, 3,6-dimethyl- (95-96-5)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 319 · H319
- Precautionary statements
- 305 · P305+P351+P338
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38-36
- Safety Statements
- 26 · 26-37/39
- WGK Germany
- 2 · 2
- RTECS
- 1100000 · JH1100000
- TSCA
- TSCA listed
- HS Code
- 29322090 · 29322090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 · Eye Irrit. 2
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
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
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
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
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-37/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H319
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2
- Precautionary statements
- P305+P351+P338
Chemistry & industry
Uses & manufacturing
General Manufacturing Information
Plastics Product Manufacturing
1,4-Dioxane-2,5-dione, 3,6-dimethyl-: ACTIVE
Applications
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
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: Lactide is a member of dioxanes.
Related reactions
Compound notes
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