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SML1149

BMS-189453

≥98% (HPLC)

Synonym(s):

(E)-4-[2-(5,6-Dihydro-5,5-dimethyl-8-phenyl-2-naphthalenyl)ethenyl]-benzoic acid, BMS-453, BMS453

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5 mg

Available to ship TODAYfromMILWAUKEE

$146.00
25 mg

Available to ship TODAYfromMILWAUKEE

$589.00

About This Item

Empirical Formula (Hill Notation):
C27H24O2
CAS Number:
166977-43-1
Molecular Weight:
380.48
NACRES:
NA.77
PubChem Substance ID:
329825683
UNSPSC Code:
12352200
MDL number:
MFCD18086870
Assay:
≥98% (HPLC)
Form:
powder

$146.00

Available to ship TODAYDetails

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Quality Segment

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

SMILES string

OC(C(C=C1)=CC=C1/C=C/C(C=C2)=CC3=C2C(C)(C)CC=C3C4=CC=CC=C4)=O

InChI

1S/C27H24O2/c1-27(2)17-16-23(21-6-4-3-5-7-21)24-18-20(12-15-25(24)27)9-8-19-10-13-22(14-11-19)26(28)29/h3-16,18H,17H2,1-2H3,(H,28,29)/b9-8+

InChI key

VUODRPPTYLBGFM-CMDGGOBGSA-N

Biochem/physiol Actions

BMS-189453 is a potent RARβ agonist that acts as an antagonist against RARα and RARγ. BMS-189453 induces RARβ reporter gene expression at sub nanomolar levels, and is 30 fold more potent than all-trans retinoic acid for inducing TGFβ activity in normal breast cells. The compound BMS-189453 does not transactivate RARα or γ transcriptional activity, but binding to those family members induces a strong transrepression of phorbol ester-induced AP-1 activity (IC50 = 0.1 nM in HeLa and MCSF-7). BMS-189453 significantly increases the efficiency of cardiac differentiation of hESCs.
BMS-189453 is a potent RARβ agonist.
BMS-189453 specifically has sufficient bioavailability in rats and monkeys. BMS-189453 only binds to α, β, and γ retinoid receptors but its activation is unknown. BMS-189453 is found to inhibit the action of collagenase-3 (MMP-13) which catalyses cartilage matrix degradation. Thus, it serves to treat rheumatoid arthritis.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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1 of 1

This Item
SML1084B6688SML2034
BMS-189453 ≥98% (HPLC)

Sigma-Aldrich

SML1149

BMS-189453

BMS-195614 ≥97% (HPLC)

Sigma-Aldrich

SML1084

BMS-195614

BMS 493 ≥98% (HPLC)

Sigma-Aldrich

B6688

BMS 493

AGN 193109 ≥98% (HPLC)

Sigma-Aldrich

SML2034

AGN 193109

description

≥98% (HPLC)

description

≥97% (HPLC)

description

≥98% (HPLC)

description

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥97% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

form

powder

form

powder

form

powder

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

solubility

DMSO: 10 mg/mL, clear

solubility

DMSO: 20 mg/mL, clear

solubility

DMSO: ≥20 mg/mL

solubility

DMSO: 2 mg/mL, clear (warmed)

color

white to beige

color

white to light brown

color

light yellow to yellow

color

white to beige

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

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Questions

  1. I didn't find the product instructions on the website, and I need to address things like how to dissolve it (SML1149).

    1 answer

    1. This product is soluble in DMSO. The exact concentration is lot-specific and reported in the Certificate of Analysis. The minimum concentration will be 10 mg/mL.

      Please see the link below to review a sample document or access a lot specific Certificate:
      https://www.sigmaaldrich.com/product/sigma/SML1149#product-documentation

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