Basic information
- CAS
12640-73-2- Standard SMILES
O=C1c2ccccc2C(=O)c2c(O)c(O)cc(O)c21- InChIKey
BBNQQADTFFCFGB-UHFFFAOYSA-N- Molecular formula
- C14H8O5
- Average molar mass
- 256.21 g/mol
- Monoisotopic mass
- 256.03717336
Overview
Purpurin is a trihydroxyanthraquinone derived from anthracene by substitution with oxo groups at C-9 and C-10 and with hydroxy groups at C-1, C-2 and C-4. It has a role as a biological pigment, a plant metabolite and a histological dye.
Names & identifiers
- Preferred name
- Purpurin anthraquinone
- IUPAC
- 1,2,4-trihydroxyanthracene-9,10-dione
- English name
- PURPURIN
- Molecular formula
- C14H8O5
- Molecular weight
- 256.21
Names & synonyms
9,10-Anthracenedione, 1,2,4-trihydroxy-purpurin anthraquinoneRefChem:46677PURPURIN81-54-91,2,4-trihydroxyanthracene-9,10-dione1,2,4-TrihydroxyanthraquinoneVerantinPurpurineHydroxylizaric acidSmoke Brown G1,2,4-Trihydroxy-9,10-anthracenedione
Show more names
CI 58205c.i.1037C.I. 1037c.i.75410NSC 10447
1,2,4-Trihydroxy-9,10-anthraquinoneC.I. 582051,2,4-TrihydroxyanthrachinonAnthraquinone, 1,2,4-trihydroxy-C.I. 75410MFCD00001203DTXSID4021214Purpurin (85%)
Database identifiers
- CAS
12640-73-2、81-54-9- PubChem CID
- 6683
- DTXSID
DTXSID4021214- ChEMBL
CHEMBL294264- ChEBI
CHEBI:8645- UNII
- L1GT81LS6N
- EC Number
- 201-359-8
- Nikkaji
- J3.859H
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 94.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 0
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 407
Experimental & physicochemical properties
Chemical ClassesDyes -> Anthraquinone Dyes
SpringerMaterials PropertiesCrystal structure
LogP1.84
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionOrange or red solid; [Merck Index] Dark brown powder; [Aldrich MSDS]
Collision Cross Section
149.0 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID4021214]
144.35 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 253 · 253-256 °C(lit.)
- Boiling point
- 359.45 °C · 359.45°C (rough estimate)
- Density
- 1.659 · 1.659
- refractive index
- 1.4825 · 1.4825 (estimate)
- Flash point
- 113 °C · 113 °C
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated)
- pka
- 7.05 · 7.05±0.20(Predicted)
- form
- Powder
- Colour Index
- 58205 · 58205
- color
- Brown-red to brown
- Water Solubility
- 6.405 mg/L · 6.405mg/L(25 ºC)
- λmax
- 515 nm521 · 515 nm521 nm (2nd)
- Merck
- 14 · 14,7945
- BRN
- 1887127 · 1887127
- Major Application
- diagnostic assay manufacturinghematologyhistology
- InChI
- 1S/C14H8O5/c15-8-5-9(16)14(19)11-10(8)12(17)6-3-1-2-4-7(6)13(11)18/h1-5,15-16,19H
- InChIKey
- BBNQQADTFFCFGB-UHFFFAOYSA-N
- SMILES
- Oc1cc(O)c2C(=O)c3ccccc3C(=O)c2c1O
- LogP
- 4.6 · 4.600 (est)
- CAS DataBase Reference
- 81 · 81-54-9
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 1 GT81LS6N · L1GT81LS6N
- EPA Substance Registry System
- Purpurin (81-54-9)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 47 · NA.47
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi,C,F
- Risk Statements
- 36 · 36/37/38-34-11
- Safety Statements
- 26 · 26-36-45-36/37/39-16
- WGK Germany
- 3 · 3
- RTECS
- 8200000 · CB8200000
- HS Code
- 29146990 · 29146990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 68 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazards SummaryA mild eye irritant; Intraperitoneal LD50 (mouse) > 500 mg/kg; [RTECS] An irritant; Targets the liver, kidney, CNS, cardiovascular system, and blood; [Aldrich MSDS] See 1,4-Dihydroxy-9,10-anthracenedione.
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- CB8200000
- hs_code
- 29146990
- risk_code
- 36/37/38-34-11
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,C,F
- safety_code
- 26-36-45-36/37/39-16
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationChemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS.
Uses & manufacturing
Uses
Formed during storage of the madder root; Forms lakes with some metal salts; Used as a fast dye for printing cotton, to make acid and chrome dyes, as a reagent for detection of boron, for histological detection of insoluble calcium salts, and as a nuclear stain; [Merck Index]
Textiles (Printing, Dyeing, or Finishing) [Category: Industry]
Applications
Usesxanthin oxidase inhibitor, irritant
UsesA xanthine oxidase inhibitor.
UsesPurpurin is a naturally occurring reddish-yellow pigment found in madder root (R. tinctorum) that has been used both in herbal remedies and as food coloring. It can also by synthetically derived from 9,10-anthraquinone. Purpurin is protective against a number of food-derived heterocyclic amines in bacterial mutagenicity assays through its inhibition of CYP450-dependent N-hydroxylation and reduction of N-hydroxylamines. Purpurine can also inhibit (IC50 = 6.6 μM) spermidine-induced autoactivation of plasma hyaluronan-binding protein, a serine protease that can activate coagulation factor VII and prourokinase.
UsesPurpurin is an anthraquinone derivative and is well known as a colour pigment derived from madder plants. Purpurin was extensively utilized in herbal remedies, in food colouring and dyes for cotton pr inting. Due to the high antioxidant activity exhibited by anthraquinone compounds, purpurin was determined through studies to possess potential radical scavenging effects. Purprin has also been shown to have inhibitory effects towards serine protease.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: A trihydroxyanthraquinone derived from anthracene by substitution with oxo groups at C-9 and C-10 and with hydroxy groups at C-1, C-2 and C-4.
Related reactions
3 records
Compound notes
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