Basic information
- CAS
1587-20-8- Standard SMILES
COC(=O)CC(O)(CC(=O)OC)C(=O)OC- InChIKey
HDDLVZWGOPWKFW-UHFFFAOYSA-N- Molecular formula
- C9H14O7
- Average molar mass
- 234.2 g/mol
- Monoisotopic mass
- 234.07395279
Overview
trimethyl citrate has been reported in Lonicera caerulea, Prunus mume, and other organisms with data available.
Names & identifiers
- Preferred name
- Trimethyl citrate
- IUPAC
- trimethyl 2-hydroxypropane-1,2,3-tricarboxylate
- English name
- Trimethyl citrate
- Molecular formula
- C9H14O7
- Molecular weight
- 234.2
Names & synonyms
Show more names
Database identifiers
- CAS
1587-20-8- PubChem CID
- 74112
- DTXSID
DTXSID2061804- ChEMBL
CHEMBL455514- UNII
- 2P8176332L
- EC Number
- 216-449-2
- Nikkaji
- J26.348F
Properties
Computed structural properties
- XLogP
- -1
- Topological polar surface area
- 99.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 8
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 266
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 75 · 75-78 °C
- Boiling point
- 176 · 176 16mm
- Density
- 1.3363 · 1.3363 (rough estimate)
- vapor pressure
- 1.3 hPa · 1.3hPa at 20℃
- refractive index
- 1.4455 · 1.4455 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Chloroform (Sparingly), Methanol (Slightly)
- form
- Solid
- pka
- 10.43 · 10.43±0.29(Predicted)
- color
- White to Off-White
- Odor
- 100 % · at 100.00 %. ethereal fruity
- Odor Type
- ethereal
- Water Solubility
- 53.2 g/L · 53.2g/L at 20℃
- BRN
- 1796169 · 1796169
- InChI
- 1S/C9H14O7/c1-14-6(10)4-9(13,8(12)16-3)5-7(11)15-2/h13H,4-5H2,1-3H3
- InChIKey
- HDDLVZWGOPWKFW-UHFFFAOYSA-N
- SMILES
- COC(=O)CC(O)(CC(=O)OC)C(=O)OC
- LogP
- 0.7 at · 0.7 at 20℃
- CAS DataBase Reference
- 1587 · 1587-20-8(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 2 P8176332L · 2P8176332L
- EPA Substance Registry System
- 1 · 1,2,3-Propanetricarboxylic acid, 2-hydroxy-, trimethyl ester (1587-20-8)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Warning
- Hazard statements
- 314 · H314
- Precautionary statements
- 264 b-P271-P280-P301+P330+P331-P304+P340-P305+P351+P338-P310-P363-P403+P233-P501c · P264b-P271-P280-P301+P330+P331-P304+P340-P305+P351+P338-P310-P363-P403+P233-P501c
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Safety Statements
- 22 · 22-24/25
- WGK Germany
- 3 · 3
- TSCA
- TSCA listed
- HS Code
- 29181500 · 29181500
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (3 of 3) of all reports.
Not Classified
Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
REACH registered substance: Trimethyl citrate (EC: 216-449-2)
1,2,3-Propanetricarboxylic acid, 2-hydroxy-, trimethyl ester: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29181500
- Signal word
- Warning
- Symbol(GHS)
- GHS05
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H314
- REACH Registrations
- Active
- Precautionary statements
- P264b-P271-P280-P301+P330+P331-P304+P340-P305+P351+P338-P310-P363-P403+P233-P501c
Chemistry & industry
Uses & manufacturing
Applications
DescriptionTrimethyl citrate is an ester of citric acid. It is a kind of non-toxic plasticizer1. Trimethyl citrate is one of the constituents of Dioscorea opposita2. The IC50 value for monoamine oxidase-B of trimethyl citrate was studied. It has various applications3: it can do the main flame retardant candle flame color, its melting point and can fully meet the flammability requirements of candle products. It can be used for the synthesis of pharmaceutical and pesticide. It can act as the main raw material for the production of citric acid hydrochloride, citric acid hydrochloride as well as the synthetic hot melt adhesive. It can also be used as the methyl methacrylate polymer a blowing agent, a stabilizer acrylamide, polyamide adhesive initiators, PVC plasticizers. It can also be used as solvent for household and II cleaner, film-former4.
UsesTrimethyl Citrate is a reagent used in the preparation of citrate-ciprofloxacin conjugates which has antibacterial activity.
General DescriptionTrimethyl citrate is one of the constituents of Dioscorea opposita. The IC50 value for monoamine oxidase-B of trimethyl citrate was studied.
Preparation methods
PreparationTrimethyl citrate is produced by direct esterification of Citric acid with Methanol using the old-fashioned method with 3% sulfuric acid and reflux to complete the esterification.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Related reactions
No reaction records under the current filter.
Compound notes
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