BRAZILIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H14O5
Molecular Weight	286.2794
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C2[C@H]3C4=CC(O)=C(O)C=C4C[C@@]3(O)COC2=C1

InChI

InChIKey=UWHUTZOCTZJUKC-JKSUJKDBSA-N

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

HIDE SMILES / InChI

Molecular Formula	C16H14O5
Molecular Weight	286.2794
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27247107 | https://www.ncbi.nlm.nih.gov/pubmed/26428849 | https://www.ncbi.nlm.nih.gov/pubmed/28497277 | https://www.ncbi.nlm.nih.gov/pubmed/28808394

Brazilin isolated from Caesalpinia sappan has long been known as a natural red pigment. Brazilin is the safe natural compound having the potential to develop as a medicinal compound with application in food, beverage, cosmetics and pharmaceutical industries. It was shown, that brazilin exerts protective effects against renal ischemia-reperfusion injury by inhibiting the NF-κB signaling pathway. In addition, was revealed, that this compound prevented hyperglycemia, renal fibrosis, and inflammation, thus ameliorating renal functional decline in diabetic mice and may be a useful treatment for diabetic nephropathy. Brazilin isolated from H. brasiletto exhibited a moderate antiproliferative activity on the human non-cancer cell line, at the same time demonstrated to have antiproliferative activity against human cancer cell lines, and thus can be a potential source of anticancer agents.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
NF-kappa B signaling pathway 87 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27247107	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Ischemia-reperfusion injury 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27247107	Preventing	Preclinical	Unknown Approved Use Unknown
Bone loss 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26428849	Preventing	Basic research	Unknown Approved Use Unknown
Diabetic nephropathy 37 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28497277	Primary	Preclinical	Unknown Approved Use Unknown
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28808394	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antiproliferative activity of Haematoxylum brasiletto H. Karst.	2017-07	28808394
Brazilin from Caesalpinia sappan heartwood and its pharmacological activities: A review.	2015-06	26194825
Brazilin Limits Inflammatory Responses through Induction of Prosurvival Autophagy in Rheumatoid Fibroblast-Like Synoviocytes.	2015	26295477
Identification of HIV-1 integrase inhibitors based on a four-point pharmacophore.	1998-11	9865384
Inhibition of human immunodeficiency virus integrase by bis-catechols.	1995-02	7726489

Patents

Sample Use Guides

In Vivo Use Guide

Treatment with brazilin (30 mg/kg, administered intravenously at 30 min prior to ischemia) led to the reversal of renal ischemia-reperfusion (I/R)-induced changes in serum creatinine (Scr) and blood urea nitrogen (BUN) levels, and also attenuated the histopathological damage induced by I/R. db/db mice: brazilin (40 mg/kg/day i.p.)

Route of Administration: Other

In Vitro Use Guide

Brazilin was used to inhibit Zn2+-mediated Aβ aggregation and alleviate its cytotoxicity. The binding properties of brazilin and Zn2+ were first probed using Fourier transform infrared (FTIR) spectroscopy and isothermal titration calorimetry (ITC) assays. Both the FTIR and ITC results have shown that brazilin is able to bind Zn2+ in a physiologically suitable range of concentrations. The dissociation constant (Kd) between brazilin and Zn2+ was about 46.0±6.8μM, which makes brazilin a potential drug model for the chelation of free Zn2+. Moreover, the higher affinity of brazilin for Aβ42 (Kd=2.5±1.6μM) than that of Zn2+ (Kd=6.2±0. 9μM), enables brazilin to sequester Zn2+ from the Aβ42-Zn2+ complex.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:30:04 GMT 2025` Edited by `admin` on `Mon Mar 31 19:30:04 GMT 2025`
Record UNII	FZ39SW1K10
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BRAZILIN

Common Name

English

C.I. 75280

Preferred Name

English

BRASILIN

Common Name

English

NSC-56652

Code

English

(6AS,11BR)-7,11B-DIHYDROBENZ(B)INDENO(1,2-D)PYRAN-3,6A,9,10(6H)-TETROL

Common Name

English

BRAZILIN [MI]

Common Name

English

C.I. NATURAL RED 24

Code

English

CI-75280

Code

English

Code System Code Type Description

WIKIPEDIA

BRAZILIN