Rhein (CED0002596)

Record Information
Version1.0
Creation Date2016-05-22 03:59:54 UTC
Update Date2026-05-14 19:30:48 UTC
Accession NumberCHEM017187
Identification
Common NameRhein
ClassSmall Molecule
Description
Rhein is an organic compound with the formula C15H8O6 and an average molecular weight of 284.22 g/mol. Rhein belongs to the anthracenecarboxylic acids and derivatives, a subclass of anthracenes within the organic compounds. It is classified under the superclass of benzenoids. Industrially, the compound is used as a biocide. It has been identified in 34 recorded sources across multiple sectors. Within electrical and electronic equipment, it is found in cell phones, capacitors, batteries, printed circuit boards, and wires and cables, among 11 other items. In the food, food processing and cookware sector, it is associated with food packaging, food preservation, the preparation of vinegar, the treatment of hops, and fermentation processes for beer. Its presence is also recorded in building and construction materials such as roofs, floors, tents or canopies, and stairs and ramps. In household cleaning and consumer products, it appears in soap detergents and perfumes within detergents and soaps, as well as tobacco smoke filters. Additionally, it is found in synthetic textiles, carpets and rugs, and medical devices. Recorded routes of exposure include oral, inhalation, and touch. At the molecular level, Rhein acts on four recorded protein targets. It serves as an inhibitor of the oxysterols receptor LXR-alpha (NR1H3), the oxysterols receptor LXR-beta (NR1H2), the polyunsaturated fatty acid 5-lipoxygenase (ALOX5), and the heat shock protein HSP 90-alpha (HSP90AA1).
Contaminant Type
  • PFAS
  • Phytotoxin
Chemical Structure
Synonyms
ValueSource
1,8-Dihydroxy-3-carboxyl anthraquinoneHMDB
1,8-Dihydroxy-3-carboxyl-9,10-anthraquinoneHMDB, MeSH
1,8-Dihydroxyanthraquinone-3-carboxylic acidHMDB
4, 5-Dihydroxyanthraquinone-2-carboxylic acidHMDB
4,5-Dihydroxy-2-anthraquinonecarboxylic acidHMDB
4,5-DiOH-anthraquinone-2-COOHHMDB
9,10-dihydro-4,5-Dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid, 9ciHMDB
9,10-dihydro-4,5-Dihydroxy-9,10-dioxo-2-anthroic acidHMDB
Cassic acidHMDB
Chrysazin-3-carboxylic acidHMDB
Dipropionyl rheinHMDB, MeSH
MonorheinHMDB
Rhein (1,8-dihydroxy-3-carboxyl anthraquinone)HMDB
Rhubarb yellowHMDB
4,5-Dihydroxyanthraquinone-2-carboxylic acidMeSH, HMDB
Chemical FormulaC15H8O6
Average Molecular Mass284.220 g/mol
Monoisotopic Mass284.032 g/mol
CAS Registry Number478-43-3
IUPAC Name4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
Traditional Namemonorhein
SMILESOC(=O)C1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O
InChI IdentifierInChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21)
InChI KeyFCDLCPWAQCPTKC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassAnthracenecarboxylic acids and derivatives
Direct ParentAnthracenecarboxylic acids
Alternative Parents
Substituents
  • Anthracene carboxylic acid
  • 9,10-anthraquinone
  • Anthraquinone
  • 2-naphthalenecarboxylic acid
  • 2-naphthalenecarboxylic acid or derivatives
  • Hydroxybenzoic acid
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Vinylogous acid
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP2.18ALOGPS
logP3.27ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.4ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity72.37 m³·mol⁻¹ChemAxon
Polarizability26.62 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-07cv-0590000000-afcf37d77e69652177f2Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-024r-4102900000-c5b546456fd0d7644f8aNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0090000000-9ac3e7791e49a21d3f7eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0090000000-8a0c3c4f77482fc05626Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0190000000-a217257577bda56ddeb9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0950000000-f5cac5a3a6c78fc4ed85Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0910000000-4671892dc0bcf7214bc0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0090000000-5f27d9cb7d81c2b3da8dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0190000000-87c468c6073faf9e5faeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0920000000-0b0038f124d8c1494117Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0090000000-a2294fd7666d75dbcbd0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052u-0890000000-5f1951e9414e26b22db9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0920000000-5757933ef5a7532b4ef1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0090000000-a2294fd7666d75dbcbd0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000l-0090000000-a2178fdd7c56081cab09Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0090000000-8f070d596b12739e117eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ac0-0910000000-a9cb6e465076d6963a82Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0090000000-2c3cbe9c71ab4af87a66Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0290000000-66c888a0ecf96ae01c8cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0920000000-eb6d2ee2a66f5ba2d590Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0090000000-467e222d330c2d39d5b1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0190000000-771535379f5c72ad9306Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kr-0090000000-6163d091b67836bcff63Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014r-0190000000-bd5d0494f66cd7d5828cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00rl-2290000000-33f58cc10ba47d1b818aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0090000000-05c98e64e03e092b3975Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0019-0090000000-ec4cf61d964a40527521Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00ku-4390000000-5d5e000d8c2e171dd309Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kr-0090000000-4e9b16f39beba140d067Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0090000000-f8f199f4dd68ee087eafNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0309-3960000000-3e29357b374cb31d3969Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0019-0090000000-5587686c2e45253790aaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001r-0090000000-af5371e45a60700f16c2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dr-0390000000-f12bd9f6034917912155Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2678.0Log mg/kg[1500:4800]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
10InsecticidesAgriculture & land managementNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
233BrushesPersonal care & cosmeticsNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
497FloorsBuilding & ConstructionNot Available
499RoofsBuilding & ConstructionNot Available
500Stairs And RampsBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
589Life BuoysMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
601Lawn MowersAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
661UmbrellasTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
DNA oxidative demethylase ALKBH2 structureClick to view 3D structureDNA oxidative demethylase ALKBH2Q6NS38HumansPredicted (SEA)0.0778492
Alpha-ketoglutarate-dependent dioxygenase FTO structureClick to view 3D structureAlpha-ketoglutarate-dependent dioxygenase FTOQ9C0B1HumansPredicted (SEA)0.389246
Click to view 3D structureAldehyde dehydrogenase, cytosolic 1P13601Rattus norvegicusPredicted (SEA)0.311397
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)42.1943
RNA demethylase ALKBH5 structureClick to view 3D structureRNA demethylase ALKBH5Q6P6C2HumansPredicted (SEA)0.0778492
Click to view 3D structureAcetylcholinesteraseO42275Electrophorus electricusPredicted (SEA)44.3741
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)72.9447
Amine oxidase [flavin-containing] A structureClick to view 3D structureAmine oxidase [flavin-containing] AP21397HumansPredicted (SEA)33.9423
Alpha-ketoglutarate-dependent dioxygenase alkB homolog 3 structureClick to view 3D structureAlpha-ketoglutarate-dependent dioxygenase alkB homolog 3Q96Q83HumansPredicted (SEA)0.0778492
Click to view 3D structureFemale germline-specific tumor suppressor gld-1Q17339Caenorhabditis elegansPredicted (SEA)0.233548
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)43.8291
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)69.3637
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)79.9511
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)69.6751
P2Y purinoceptor 12 structureClick to view 3D structureP2Y purinoceptor 12Q9H244HumansPredicted (SEA)7.16213
Cytochrome P450 1B1 structureClick to view 3D structureCytochrome P450 1B1Q16678HumansPredicted (SEA)22.4984
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)30.5169
M-phase inducer phosphatase 2 structureClick to view 3D structureM-phase inducer phosphatase 2P30305HumansPredicted (SEA)2.10193
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)46.3203
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)48.5001
Induced myeloid leukemia cell differentiation protein Mcl-1 structureClick to view 3D structureInduced myeloid leukemia cell differentiation protein Mcl-1Q07820HumansPredicted (SEA)55.6622
Click to view 3D structureCarbonic anhydraseQ2PCB5Dicentrarchus labraxPredicted (SEA)0.700643
Transthyretin structureClick to view 3D structureTransthyretinP02766HumansPredicted (SEA)16.6597
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)348.687
Click to view 3D structureHexokinase HKDC1Q2TB90HumansPredicted (SEA)6.85073
Concentrations
Not Available
External Links
DrugBank IDDB13174
HMDB IDHMDB0032876
FooDB IDFDB010856
Phenol Explorer IDNot Available
KNApSAcK IDC00002861
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDRHN
Wikipedia LinkRhein
Chemspider ID9762
ChEBI IDNot Available
PubChem Compound ID10168
Kegg Compound IDC10401
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Didry N, Dubreuil L, Pinkas M: Activity of anthraquinonic and naphthoquinonic compounds on oral bacteria. Pharmazie. 1994 Sep;49(9):681-3.
2. Stermitz FR, Cashman KK, Halligan KM, Morel C, Tegos GP, Lewis K: Polyacylated neohesperidosides from Geranium caespitosum: bacterial multidrug resistance pump inhibitors. Bioorg Med Chem Lett. 2003 Jun 2;13(11):1915-8.
3. Izzo AA, Mascolo N, Capasso F: Effect of sodium rhein on electrically-evoked and agonist-induced contractions of the guinea-pig isolated ileal circular muscle. Br J Pharmacol. 1998 Jun;124(4):825-31.
4. Kuo PL, Hsu YL, Ng LT, Lin CC: Rhein inhibits the growth and induces the apoptosis of Hep G2 cells. Planta Med. 2004 Jan;70(1):12-6.
5. Chang CY, Chan HL, Lin HY, Way TD, Kao MC, Song MZ, Lin YJ, Lin CW: Rhein induces apoptosis in human breast cancer cells. Evid Based Complement Alternat Med. 2012;2012:952504. doi: 10.1155/2012/952504. Epub 2011 Oct 5.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.