(2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid

Product Name: (2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid
CAS No.: 496868-77-0
Chemical Name: (2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid
Synonyms: ST 1926;Adarotene;Adarotene (ST1926);ST 1926;ST-1926;ST1926;Adarotene, 10 mM in DMSO;ADAROTENE;ST 1926;ST-1926;ST1926;Inhibitor,inhibit,Apoptosis,ST-1926,ST 1926,Adarotene;(E)-3-[4-[3-(1-adamantyl)-4-hydroxyphenyl]phenyl]prop-2-enoic acid;(2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid;2-Propenoic acid, 3-(4'-hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-, (2E)-
CBNumber: CB42614326
Molecular Formula: C25H26O3
Formula Weight: 374.47
MOL File: 496868-77-0.mol

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(2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid Property

Melting point:: >240 °C
Boiling point:: 574.1±50.0 °C(Predicted)
Density: 1.257
storage temp.: Store at -20°C
solubility: ≥37.4 mg/mL in DMSO; insoluble in H2O; ≥10.97 mg/mL in EtOH with gentle warming and ultrasonic
form: solid
pka: -95.54±0.10(Predicted)
color: White to green

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 29807
Product name: Adarotene
Packaging: 5mg
Price: $68
Updated: 2024/03/01

Cayman Chemical

Product number: 29807
Product name: Adarotene
Packaging: 10mg
Price: $121
Updated: 2024/03/01

Cayman Chemical

Product number: 29807
Product name: Adarotene
Packaging: 25mg
Price: $286
Updated: 2024/03/01

Cayman Chemical

Product number: 29807
Product name: Adarotene
Packaging: 50mg
Price: $535
Updated: 2024/03/01

ApexBio Technology

Product number: A3143
Product name: Adarotene
Packaging: 5mg
Price: $68
Updated: 2021/12/16

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(2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid Chemical Properties,Usage,Production

Uses

Adarotene has been found to have antitumor activity against different types of cancer, including acute myeloid leukemia, primary effusion lymphoma, prostate cancer and glioma. It may also be useful in treating acute lung injury through inflammation and ROS suppression via inactivating TLR4?/NF-?κB and p38?/ERK1?/2 signaling pathways.

Biological Activity

ST1926 is an atypical retinoid th at is able to overcome resistance to ATRA. ST1926 appears to induce apoptosis by production of DNA double-strand breaks (DSB) and chromosomal lesions during the S phase of the cell cycle.', 'ST1926 is considered to be more apoptotic than CD437. It is much effective in mobilizing calcium than CD437. ST1926 repress toll-like receptor 4 (TLR4)/myeloid differentiation factor 88 (MyD88) signal pathway to disable the actions of nuclear factor-KB (NF-KB). It has the ability to repress inflammation response and ROS synthesis in lung epithelial cells in vitro.

Synthesis

496858-32-3

496868-77-0

General procedure for the synthesis of (E)-3-(3'-(adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid from methyl (E)-3-(3'-(adamantan-1-yl)-4'-hydroxy-[1,1'-biphenylyl]-4-yl)propenoate: the (E )-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid methyl ester (3.28 g, 8.45 mmol) was added to a solution of LiOH-H2O (1.77 g, 42.25 mmol) in 340 mL of THF/H2O (1:1) and the mixture was stirred at room temperature overnight. After evaporation of THF, the mixture was extracted with hexane, acidified with 2N HCl and filtered to give 2.82 g (94%) of (E)-3-(3'-(adamantan-1-yl)-4'-hydroxy-[1,1'-biphenylyl]-4-yl)propenoic acid with a melting point of > 240 °C. 1H NMR (DMSO-d6): δ 1.74 (6H, s, 6Ad), 2.04 (3H, s, 3Ad), 2.12 (6H, s, 6Ad), 6.51 (1H, d, -CH, J=16.1Hz), 6.85 (1H, d, 1Ar, J=8.8Hz), 7.30-7.40 (2H, m, 2Ar). 7.55-7.63 (3H, m, 2Ar + CH), 7.70 (2H, d, 2Ar, J=8.0Hz), 9.54 (1H, s, -OH), 12.34 (1H, brs, -COOH).MS (m/z): 374 (M+, 100).

in vivo

Adarotene (15, 20 mg/kg, p.o.) causes a significant tumor growth inhibition in a human ovarian carcinoma, A2780/DX, and in a human melanoma, MeWo, growing in nude mice^[1]. Adarotene (30, 40 mg/kg, p.o.) results in a significant and dose-dependent increase in the life span of NB4-bearing SCID mice without overt toxicity^[2].

target

RAR β

References

[1] Journal of Medicinal Chemistry, 2003, vol. 46, # 6, p. 909 - 912
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 15, p. 4931 - 4946
[3] European Journal of Medicinal Chemistry, 2014, vol. 79, p. 251 - 259

(2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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(2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid Suppliers

China 77 India 1 United States 10 Global 88

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View Lastest Price from (2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid manufacturers

Career Henan Chemical Co

Product: (2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid 496868-77-0
Price: US $1.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 1lg; 2kg; 5kg; 10kg; 100kg
Release date: 2019-08-31

496868-77-0, (2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acidRelated Search:

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ST 1926;ST-1926;ST1926

Adarotene (ST1926)

(E)-3-[4-[3-(1-adamantyl)-4-hydroxyphenyl]phenyl]prop-2-enoic acid

ADAROTENE;ST 1926;ST-1926;ST1926

(2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid

Adarotene

ST 1926

2-Propenoic acid, 3-(4'-hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-, (2E)-

Inhibitor,inhibit,Apoptosis,ST-1926,ST 1926,Adarotene

Adarotene, 10 mM in DMSO

496868-77-0