Brazilin

Brazilin
Names
	Preferred IUPAC name (6aS,11bR)-7,11b-Dihydroindeno[2,1-c][1]benzopyran-3,6a,9,10(6H)-tetrol
	Other names Brasilin; Natural Red 24; CI 75280
Identifiers
CAS Number	474-07-7 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	4198570
ChEBI	CHEBI:3170 ;
ChEMBL	ChEMBL598951 ;
ChemSpider	66104 ;
ECHA InfoCard	100.006.799
EC Number	207-477-6;
KEGG	C09920;
PubChem CID	73384;
UNII	FZ39SW1K10 ;
CompTox Dashboard (EPA)	DTXSID80883393 ;
	InChI InChI=1S/C16H14O5/c17-9-1-2-10-14(4-9)21-7-16(20)6-8-3-12(18)13(19)5-11(8)15(10)16/h1-5,15,17-20H,6-7H2/t15-,16+/m0/s1 Key: UWHUTZOCTZJUKC-JKSUJKDBSA-N ; InChI=1/C16H14O5/c17-9-1-2-10-14(4-9)21-7-16(20)6-8-3-12(18)13(19)5-11(8)15(10)16/h1-5,15,17-20H,6-7H2/t15-,16+/m0/s1 Key: UWHUTZOCTZJUKC-JKSUJKDBBS;
	SMILES C1C2=CC(=C(C=C2[C@H]3[C@@]1(COC4=C3C=CC(=C4)O)O)O)O; Oc1cc3c(cc1O)[C@@H]2c4c(OC[C@]2(O)C3)cc(O)cc4;
Properties
Chemical formula	C16H14O5
Molar mass	286.283 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Brazilin is a naturally occurring, homoisoflavonoid, red dye obtained from the wood of Paubrasilia echinata, Biancaea sappan, Caesalpinia violacea, and Haematoxylum brasiletto (also known as Natural Red 24 and CI 75280).^[1] Brazilin has been used since at least the Middle Ages to dye fabric, and has been used to make paints and inks as well. The specific color produced by the pigment depends on its manner of preparation: in an acidic solution brazilin will appear yellow, but in an alkaline preparation it will appear red. Brazilin is closely related to the blue-black dye precursor hematoxylin, having one fewer hydroxyl group. Brazilein, the active dye agent, is an oxidized form of brazilin.^[2]^[1]

^ ^a ^b Dapson RW, Bain CL (2015). "Brazilwood, sappanwood, brazilin and the red dye brazilein: from textile dyeing and folk medicine to biological staining and musical instruments". Biotech Histochem. 90 (6): 401–23. doi:10.3109/10520295.2015.1021381. PMID 25893688.
^ De Oliveira, Luiz F.C.; Edwards, Howell G.M.; Velozo, Eudes S.; Nesbitt, M. (2002). "Vibrational spectroscopic study of brazilin and brazilein, the main constituents of brazilwood from Brazil". Vibrational Spectroscopy. 28 (2): 243. doi:10.1016/S0924-2031(01)00138-2.

[Dapson_and_Bain,_2015-1] Dapson RW, Bain CL (2015). "Brazilwood, sappanwood, brazilin and the red dye brazilein: from textile dyeing and folk medicine to biological staining and musical instruments". Biotech Histochem. 90 (6): 401–23. doi:10.3109/10520295.2015.1021381. PMID 25893688.

[2] De Oliveira, Luiz F.C.; Edwards, Howell G.M.; Velozo, Eudes S.; Nesbitt, M. (2002). "Vibrational spectroscopic study of brazilin and brazilein, the main constituents of brazilwood from Brazil". Vibrational Spectroscopy. 28 (2): 243. doi:10.1016/S0924-2031(01)00138-2.

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