Basic information
- CAS
517-28-2- Standard SMILES
Oc1cc2c(cc1O)[C@@H]1c3ccc(O)c(O)c3OC[C@]1(O)C2- InChIKey
WZUVPPKBWHMQCE-XJKSGUPXSA-N- Molecular formula
- C16H14O6
- Average molar mass
- 302.28 g/mol
- Monoisotopic mass
- 302.07903817
Overview
Hematoxylin appears as white to yellowish crystals that redden on exposure to light. (NTP, 1992)
Names & identifiers
- Preferred name
- Hematoxylin
- IUPAC
- (6aS,11bR)-7,11b-dihydro-6H-indeno[2,1-c]chromene-3,4,6a,9,10-pentol
- English name
- Logwood extract
- Molecular weight
- 0
Names & synonyms
HEMATOXYLIN517-28-2HaematoxylinHydroxybrazilinHydroxybrasilinNatural Black 1(+)-HematoxylinHydroxylrasilinDTXSID8020678YKM8PY2Z55(6aS,11bR)-7,11b-dihydro-6H-indeno[2,1-c]chromene-3,4,6a,9,10-pentolBenz(b)indeno(1,2-d)pyran-3,4,6a,9,10(6H)-pentol, 7,11b-dihydro-, cis-(+)-
Show more names
C.I. Natural Black 1Hematoksylinhaematoxylum campechianum wood extractHAEMATOXYLON CAMPECHIANUM WOOD EXTRACT
CHEBI:5601hematoxilineC.I. 75290NSC-270085Hemotoxylincis-(+)-7,11b-dihydrobenz[b]indeno[1,2-d]pyran-3,4,6a,9,10(6H)-pentolCHEBI:51686(6aS,11bR)-7,11b-dihydro-6H-indeno(2,1-c)chromene-3,4,6a,9,10-pentol
Database identifiers
- CAS
517-28-2、8005-33-2- PubChem CID
- 442514
- DTXSID
DTXSID8020678- ChEMBL
CHEMBL1479103、CHEMBL477197- ChEBI
CHEBI:5601
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 110 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 0
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 444
Experimental & physicochemical properties
Chemical ClassesDyes -> Other Dyes
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Neoflavonoids [PK1210]
CosmeticsAstringent; Antimicrobial
Food AdditivesDrugs -> FDA Regulatory Status of Color Additives
SolubilitySlightly soluble in cold; soluble in hot (NTP, 1992)
Melting Point212 to 248 °F (NTP, 1992)
Optical RotationSPECIFIC OPTICAL ROTATION: +11 (WATER, 3.7%); MAX ABSORPTION (0.1 N KOH): 499 NM, 534.4 NM, 565 NM, 615.5 NM
Physical Description
Hematoxylin appears as white to yellowish crystals that redden on exposure to light. (NTP, 1992)
Trihydrate: White to yellowish solid; Turns red when exposed to light; [Merck Index] Slightly beige powder; [MSDSonline]
Stability/Shelf LifeTURNS RED ON EXPOSURE TO LIGHT; ITS SOLN DARKEN ON STANDING /TRIHYDRATE/
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 5% (3 of 60) of reports.
Warning
H302 (76.7%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, 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 60 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benz[b]indeno[1,2-d]pyran-3,4,6a,9,10(6H)-pentol, 7,11b-dihydro-, cis-(+)-
Chemical: C.I. Natural Black 1
Status: Active Update: 01-04-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/28003
Hematoxylin: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryAn irritant; May be harmful if ingested; Do not breathe dust; [MSDSonline]
Reactive GroupPhenols and Cresols
Reactivity ProfileSensitive to light. (NTP, 1992).
Air and Water ReactionsSoluble in hot water, slightly water soluble in cold (NTP, 1992).
Hazard Classes and CategoriesAcute Tox. 4 (76.7%)
Safety & protection
Chemistry & industry
Pharmacology
Mechanism of ActionBRAZILIN, TOGETHER WITH HEMATOXYLIN, A CONSTITUENT OF HAEMATOXYLON CAMPECHIANUM WOOD, EXHIBITED ANTIINFLAMMATORY ACTIVITIES IN CARRAGEENIN-INDUCED RAT PAW EDEMA TEST & FERTILE EGG TEST.
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
Found in the heart-wood of logwood; Used as microscopy stain and to make inks; [Merck Index]
BIOLOGICAL STAIN IN MICROSCOPY, EG, HISTOLOGY; MFR OF INKS
U.S. Exports
(1977) No Data
(1979) No Data
U.S. Imports
(1977) No Data
(1979) No Data
U.S. Production
(1977) NOT PRODUCED COMMERCIALLY IN US
(1979) NOT PRODUCED COMMERCIALLY IN US
Methods of Manufacturing
EXTRACTED FROM THE HEART-WOOD OF THE TREE HAEMATOXYLON CAMPECHIANUM L., LEGUMINOSAE (LOGWOOD)
SYNTH: DANN, HOFMAN, ANGEW CHEM 75, 1125 (1963); MORSINGH, ROBINSON, TETRAHEDRON 26, 281 (1970)...
Use ClassificationCosmetics -> Astringent; Antimicrobial
General Manufacturing Information
Benz[b]indeno[1,2-d]pyran-3,4,6a,9,10(6H)-pentol, 7,11b-dihydro-, (6aS,11bR)-: ACTIVE
C.I. Natural Black 1: INACTIVE
Related reactions
1 records
Compound notes
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