Basic information
- CAS
499-12-7- Standard SMILES
O=C(O)/C=C(/CC(=O)O)C(=O)O- InChIKey
GTZCVFVGUGFEME-IWQZZHSRSA-N- Molecular formula
- C6H6O6
- Average molar mass
- 174.11 g/mol
- Monoisotopic mass
- 174.01643791
Overview
Cis-aconitic acid is the cis-isomer of aconitic acid. It has a role as a fundamental metabolite. It is a conjugate acid of a cis-aconitate(3-).
Names & identifiers
- Preferred name
- cis-Aconitic acid
- IUPAC
- (Z)-prop-1-ene-1,2,3-tricarboxylic acid
- English name
- cis-Aconitic acid
- Molecular formula
- C6H6O6
- Molecular weight
- 174.11
Names & synonyms
cis-Aconitic acid585-84-2cis-aconitate(Z)-prop-1-ene-1,2,3-tricarboxylic acid(1Z)-prop-1-ene-1,2,3-tricarboxylic acid(Z)-Aconitic acidcis-Aconic acid(Z)-1-Propene-1,2,3-tricarboxylic acidcis-Oxaloacetic acidAconitic acid, cis-Aconitic acid, (Z)-NSC 7616
Show more names
(1E)-prop-1-ene-1,2,3-tricarboxylic acidFEMA 2010NSC 227901cis-aconiticCls-Aconitic acidcis-Citridic acid
cis-1-propene-1,2,3-tricarboxylic acidMFCD00063184propene-1,2,3-tricarboxylicacid1-Propene-1,2,3-tricarboxylic acid, (1Z)-OF5471ZHRRCHEMBL347285(1Z)-1-Propene-1,2,3-tricarboxylic acidprop-1-ene-1,2,3-tricarboxylic acid
Database identifiers
- CAS
499-12-7、585-84-2- PubChem CID
- 643757
- DTXSID
DTXSID30883449- ChEMBL
CHEMBL347285- ChEBI
CHEBI:32805- UNII
- OF5471ZHRR
- EC Number
- 209-564-4
- Nikkaji
- J37.488A、J71.033D
Properties
Computed structural properties
- XLogP
- -1
- Topological polar surface area
- 112 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 4
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 251
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP-0.140
Solubility400.0 mg/mL
Boiling Point542.00 to 543.00 °C. @ 760.00 mm Hg
Melting Point125 °C
Physical DescriptionSolid
Collision Cross Section152.21 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
Physicochemical properties
- Melting point
- 122 °C · 122 °C (lit.)
- Boiling point
- 225.05 °C · 225.05°C (rough estimate)
- Density
- 1.66 · 1.660
- refractive index
- 1.586 · 1.5860 (estimate)
- FEMA
- 2010 · 2010 | ACONITIC ACID
- storage temp.
- -20 °C · -20°C
- solubility
- Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 1.95 · 1.95(at 25℃)
- color
- White to Off-White
- PH
- 3.05 · 3.05(1 mM solution);2.21(10 mM solution);1.55(100 mM solution)
- Odor
- bland
- Water Solubility
- Soluble in water, alcohol. Slightly soluble in ether.
- BRN
- 1725829 · 1725829
- Stability
- Hygroscopic, Light Sensitive
- InChI
- 1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1-
- InChIKey
- GTZCVFVGUGFEME-IWQZZHSRSA-N
- SMILES
- OC(=O)C\C(=C\C(O)=O)C(O)=O
- LogP
- -0.14 · -0.14
- CAS DataBase Reference
- 585 · 585-84-2(CAS DataBase Reference)
- FDA UNII
- 5471 ZHRR · OF5471ZHRR
- EPA Substance Registry System
- 1 · 1-Propene-1,2,3-tricarboxylic acid, (1Z)- (585-84-2)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 315 · H315-H319-H335-H350
- Precautionary statements
- 202 · P202-P261-P264-P302+P352-P305+P351+P338-P308+P313
- target organs
- Respiratory system
- Hazard Codes
- Xn,Xi
- Risk Statements
- 36 · 36/38-40-36/37/38
- Safety Statements
- 26 · 26-36/37-36
- WGK Germany
- 1 · 1
- F
- 3 · 3
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 2917198090 · 2917198090
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 1 BEye · Carc. 1BEye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 33.3% (3 of 9) of reports.
Warning
H302 (11.1%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 9 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (66.7%)
Safety data
- F
- 3
- wgk
- 1
- tsca
- TSCA listed
- hs_code
- 2917198090
- risk_code
- 36/38-40-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 26-36/37-36
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335-H350
- Hazard Classifications
- Carc. 1BEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P202-P261-P264-P302+P352-P305+P351+P338-P308+P313
Chemistry & industry
Pharmacology
Tissue LocationsProstate
Cellular LocationsCytoplasm
Metabolite Pathways2-ketoglutarate dehydrogenase complex deficiency
Uses & manufacturing
General Manufacturing Information1-Propene-1,2,3-tricarboxylic acid, (1Z)-: ACTIVE
Applications
Usescis-Aconitic acid is used as an intermediate in the production of substances pharmaceuticals. It is widely used in chemical research and as reagent. It acts as a cis-isomer of aconitic acid.
Usescis-Aconitic acid can be used as a standard for the determination of organic acids in plant tissues.
Usescis-Aconitic Acid is the cis-isomer of Aconitic Acid. The conjugate base of cis-Aconitic Acid is an intermediate in the isomerization of citrate and isocitrate in the citric acid cycle.
General DescriptionThis substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG
Upstream & downstream products
Upstream raw materials
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Additional notes
DefinitionChEBI: The cis-isomer of aconitic acid.
Related reactions
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Compound notes
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