Hematoxylin
Athanor · official
C16H14O6 · 302.28 g/mol
IUPAC name: (6aS,11bR)-7,11b-dihydro-6H-indeno[2,1-c]chromene-3,4,6a,9,10-pentol
Also called haematoxylin, H&E stain, natural black 1, nuclear stain
WarningHarmful if swallowed · Causes skin irritation · Causes serious eye irritation · May cause respiratory irritationNames and identifiers
- IUPAC name
- (6aS,11bR)-7,11b-dihydro-6H-indeno[2,1-c]chromene-3,4,6a,9,10-pentol
- Synonyms
- haematoxylin, H&E stain, natural black 1
+ 38 more
nuclear stain, Haematoxylin, Hydroxybrazilin, Hydroxybrasilin, Natural Black 1, (+)-Hematoxylin, Hydroxylrasilin, DTXSID8020678, YKM8PY2Z55, (6aS,11bR)-7,11b-dihydro-6H-indeno[2,1-c]chromene-3,4,6a,9,10-pentol, Benz(b)indeno(1,2-d)pyran-3,4,6a,9,10(6H)-pentol, 7,11b-dihydro-, cis-(+)-, CHEBI:5601, hematoxiline, C.I. 75290, NSC-270085, Hemotoxylin, cis-(+)-7,11b-dihydrobenz[b]indeno[1,2-d]pyran-3,4,6a,9,10(6H)-pentol, CHEBI:51686, (6aS,11bR)-7,11b-dihydro-6H-indeno(2,1-c)chromene-3,4,6a,9,10-pentol, cis-(+)-7,11b-dihydrobenz(b)indeno(1,2-d)pyran-3,4,6a,9,10(6H)-pentol, RefChem:783504, DTXCID101777594, 208-237-3, 7,11b-dihydro-6H-indeno(2,1-c)chromene-3,4,6a,9,10-pentol, BENZ(B)INDENO(1,2-D)PYRAN-3,4,6A,9,10(6H)-PENTOL, 7,11B-DIHYDRO-, Hematoxylin hydrate, (+)-haematoxylin, HSDB 4174, NSC 270085, Hematoxylin (Technical Grade), CHEMBL477197, NCI-C55889, (6aS,11bR)-6,6a,7,11b-tetrahydroindeno[2,1-c]chromene-3,4,6a,9,10-pentaol, LMPK12100063, NCGC00160144-01, (6aS,11bR)-7,11b-dihydrobenz[b]indeno[1,2-d]pyran-3,4,6a,9,10(6H)-pentol, hematoxilina, Benz[b]indeno[1,2-d]pyran-3,4,6a,9,10(6H)-pentol, 7,11b-dihydro-,(6aS,11bR)-
- Molecular formula
- C16H14O6
- Empirical formula
- C8H7O3
- Molecular weight
- 302.28 g/mol
- Exact mass
- 302.07904
- CAS number
- 517-28-2
- PubChem CID
- 442514
- Canonical SMILES
- C1C2=CC(=C(C=C2C3C1(COC4=C3C=CC(=C4O)O)O)O)O
- Isomeric SMILES
- C1C2=CC(=C(C=C2[C@H]3[C@@]1(COC4=C3C=CC(=C4O)O)O)O)O
- InChI
- InChI=1S/C16H14O6/c17-10-2-1-8-13-9-4-12(19)11(18)3-7(9)5-16(13,21)6-22-15(8)14(10)20/h1-4,13,17-21H,5-6H2/t13-,16+/m0/s1
- InChIKey
- WZUVPPKBWHMQCE-XJKSGUPXSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Physical properties
- Appearance
- Hematoxylin appears as white to yellowish crystals that redden on exposure to light. (NTP, 1992)[1]
- Melting point
- 100 to 120 °C (212 to 248 °F, NTP 1992)[1]
- Solubility in water
- Slightly soluble in cold; soluble in hot (NTP, 1992)[1]
Each value as its source reports it, with the source's number after it (listed under References). Where several sources report a property, the row shows the value most of them agree on, the rule the app uses; open the values to see every one.
Calculated
- Heavy atoms
- 22
- Rings
- 4
- Aromatic rings
- 2
- Fraction sp³ carbons (Fsp3)
- 0.25
- H-bond donors
- 5
- H-bond acceptors
- 6
- Rotatable bonds
- 0
- TPSA (Ų)
- 110.4 computed here · PubChem 110
- Formal charge
- 0
- XLogP3
- 1.2 PubChem
- Complexity
- 444 PubChem
- Stereocenters
- 0 defined, 2 undefinedCIP: C2: undefined · C13: undefined
- Double-bond geometry
- None specified
- Point group
- C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)
Elemental analysis
- C63.58%
- H4.67%
- O31.76%
Isotope pattern
Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.
Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.
Predicted
- log P
- 1.32 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -2.95 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 3.8 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 302.28
- log P ≤ 5 (Crippen): 1.32
- H-bond donors ≤ 5: 5
- H-bond acceptors ≤ 10: 6
Passes all four rules.
¹³C NMR shifts, predicted
Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.
Safety
Warning
Most widely reported: 60 company reports to ECHA. Source [2].
- Harmful or irritant
- H302Harmful if swallowed (76.7% of reports)
- H315Causes skin irritation (93.3% of reports)
- H319Causes serious eye irritation (93.3% of reports)
- H335May cause respiratory irritation (90% of reports)
Precautionary statements: 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, P501
View all classifications (2)
- [2] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 5% (3 of 60) of reports.
- [2] European Chemicals Agency (ECHA) · 60 reports · WarningH302, H315, H319, H335
First aid
- Eyes: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. Immediately transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. Skin: Immediately flood affected skin with water while removing and isolating all contaminated clothing.[1]
Safety data sheets on the supplier’s page: Accel Scientific, eMolecules, Accela ChemBio Inc..
Always read the supplier’s safety data sheet before working with it.
Spectra
Experimental spectra held by these sources; each link opens the source's own record.
Literature
Reading PubChem, OpenAlex and GSRS…
Bioactivity
Reading ChEMBL…
References
- [1]CAMEO Chemicals · Public domain (NOAA) · via PubChem · retrieved 2026-10-14
- [2]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
- [3]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.