Djenkolic acid
Basic information
- CAS
498-59-9- Standard SMILES
N[C@@H](CSCSC[C@H](N)C(=O)O)C(=O)O- InChIKey
JMQMNWIBUCGUDO-WHFBIAKZSA-N- Molecular formula
- C7H14N2O4S2
- Average molar mass
- 254.3 g/mol
- Monoisotopic mass
- 254.03949928
Overview
L-djenkolic acid is a dithioacetal consisting of two molecules of L-cysteine joined via their sulfanyl groups to methylene. It has a role as a toxin and a plant metabolite. It is a dithioacetal, a non-proteinogenic L-alpha-amino acid and a L-cysteine derivative.
Names & identifiers
- Preferred name
- Djenkolic acid
- IUPAC
- (2R)-2-amino-3-[[(2R)-2-amino-2-carboxyethyl]sulfanylmethylsulfanyl]propanoic acid
- English name
- Djenkolic acid
- Molecular formula
- C7H14N2O4S2
- Molecular weight
- 254.33
Names & synonyms
Djenkolic acid498-59-9L-Djenkolic acidbeta,beta'-MethylenedithiodialanineL-Cysteine thioacetal of formaldehyde3,3'-(Methylenedithio)dialanines,s'-methylenebis-l-cysteine3QHC9R0YFZ3,3'-Methylenedithiobis(2-aminopropanoic acid)CHEBI:6211DTXSID80198075NSC-76076
Show more names
Djenkolicjenkolic acidjengkolic acidDJENKOLIC ACID, L-Djenkolic Acid >S,S'-MethylenebiscysteineL-S,S'-METHYLENEDICYSTEINE
2-amino-3-((((2-amino-2-carboxyethyl)sulfanyl)methyl)sulfanyl)propanoic acidRefChem:920540DTXCID10120566207-863-4DjenkolateL-DjenkolateS,S'-Methylenedi-L-cysteineS,S'-Methylenebis[L-cysteine]
Database identifiers
- CAS
498-59-9- PubChem CID
- 68134
- DTXSID
DTXSID80198075- ChEMBL
CHEMBL3138615- ChEBI
CHEBI:6211
Properties
Computed structural properties
- XLogP
- -5.6
- Topological polar surface area
- 177 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 8
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 205
Physicochemical properties
- Melting point
- 325 °C · 325°C (rough estimate)
- Boiling point
- 515.4 · 515.4±50.0 °C(Predicted)
- alpha
- 20.5 · D20.5 -65.0° (1.0N HCl); D25 -47.5° (c = 2 in 1.0N HCl)
- Density
- 1.4799 · 1.4799 (rough estimate)
- refractive index
- -65 ° · -65 ° (C=1, 1mol/L HCl)
- storage temp.
- 2 · 2-8°C
- solubility
- 0.1 · DMSO:0.1(Max Conc. mg/mL);0.39(Max Conc. mM)Water:25.0(Max Conc. mg/mL);98.3(Max Conc. mM)
- form
- Solid
- pka
- 1 · pK1:2.200(＋1);pK2:8.16(0) (25°C)
- color
- White to off-white
- Water Solubility
- 5 g/L · 5g/L(100 ºC)
- Merck
- 14 · 14,3387
- CAS DataBase Reference
- 498 · 498-59-9(CAS DataBase Reference)
- FDA UNII
- 3 QHC9R0YFZ · 3QHC9R0YFZ
- Symbol(GHS)
- 7 · GHS07
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
TreatmentTreatment for djenkolic acid poisoning requires hydration to increase urine flow and alkalinization of urine by sodium bicarbonate. (L1236)
Health EffectsDjenkolic acid is nephrotoxic to humans. (L1236)
Exposure RoutesOral (ingestion) (L1817) ; dermal (L1817)
Toxicity Summary
The toxicity of djenkolic acid in humans arises from its poor solubility under acidic conditions after consumption of the jenkol bean. The amino acid precipitates into crystals which cause mechanical irritation of the renal tubules and urinary tract. (L1236)
Signs and Symptoms
Symptoms of djenkolic acid poisoning include abdominal discomfort, loin pains, severe colic, nausea, vomiting, dysuria, gross hematuria, and oliguria. Urolithiasis can also happen, with djenkolic acid as the nucleus. In young children it has also been reported to produce painful swelling of the genitalia. (L1236)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- hs_code
- 2930909899
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P271-P280
Chemistry & industry
Uses & manufacturing
UsesDjenkolic acid is a plant toxin found in the beans of the South-East Asian legumes jengkol (Archidendron jiringa). (L1236)
Applications
UsesDjenkolic Acid can be used as a pharmaceutical composition consisting of cannabinoid.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: A dithioacetal consisting of two molecules of L-cysteine joined via their sulfanyl groups to methylene.
Suppliers
Loading…
Open inquiries
Loading…
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…