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550-24-3

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550-24-3 Usage

Description

Embelin (550-24-3) inhibits?the lysine acetyl transferase PCAF?in vitro and in vivo?(in vitro?IC50=7.2 mM). Inhibits H3K9 acetylation in mouse liver tissue while leaving levels of H3K14, H4K8, H4K12 unchanged.1? Also inhibits X-linked inhibitor of apoptosis (XIAP) (IC50 = 4.1 μM, competing with Smac peptide). Binds to the BIR3 domain, preventing XIAP interaction with caspase-9 and Smac. Induces apoptosis and alters gene expression profiles in breast cancer cells.3?Possesses anti-inflammatory and analgesic activity?in vivo.4?Cell-permeable.

Chemical Properties

Orange Solid

Uses

Different sources of media describe the Uses of 550-24-3 differently. You can refer to the following data:
1. Embelin is a natural benzoquinone found in plants of the Myrsinaceae family. Embelin has a wide range of biological activity as it inhibits the growth of bacteria, fungi, protozoa and parasites. Embel in also displays contraceptive and pro-apoptotic properties.
2. Embelin is a natural benzoquinone found in plants of the Myrsinaceae family. Embelin has a wide range of biological activity as it inhibits the growth of bacteria, fungi, protozoa and parasites. Embelin also displays contraceptive and pro-apoptotic properties.

Definition

ChEBI: A member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxy-1,4-benzoquinone which is substituted by an undecyl group at position 3. Isolated from Lysimachia punctata and Embelia ribes, it exhibits antimicrobial, an ineoplastic and inhibitory activity towards hepatitis C protease.

Biological Activity

Cell-permeable, non-peptide inhibitor of X-linked inhibitor of apoptosis (XIAP) (IC 50 = 4.1 μ M in competition binding assay with Smac peptide); binds to the BIR3 domain, preventing XIAP interaction with caspase-9 and Smac. Inhibits cell growth, induces apoptosis and activates caspase-9 in prostate cancer cells (IC 50 4-6 μ M), but has a weaker effect on normal prostate cells (IC 50 = 19-20 μ M). Overcomes the protective effect of XIAP on apoptosis in XIAP-transfected Jurkat cells. Anti-tumor, analgesic and anti-inflammatory in vivo .

References

1) Modak?et al. (2013),?Probing p300/CBP associated factor (PCAF)-dependent pathways with a small molecule inhibitor; ACS Chem. Biol.,?8?1311 2) Nikolovska-Coleska?et al. (2004),?Discovery of embelin as a cell-permeable, small-molecular weight inhibitor of XIAP through structure-based computational screening of a traditional herbal medicine three-dimensional structure database; J. Med. Chem.,?47?2430 3) Shah?et al.?(2016),?Embelin inhibits proliferation, induces apoptosis and alters gene expression profiles in breast cancer cells; Pharmacol. Rep.,?68?638 4) Chitra?et al. (1994),?Antitumor, anti-inflammatory and analgesic property of embelin, a plant product.; Chemotherapy,?40?109

Check Digit Verification of cas no

The CAS Registry Mumber 550-24-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 0 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 550-24:
(5*5)+(4*5)+(3*0)+(2*2)+(1*4)=53
53 % 10 = 3
So 550-24-3 is a valid CAS Registry Number.
InChI:InChI=1/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3

550-24-3 Well-known Company Product Price

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  • Sigma

  • (E1406)  Embelin  ≥98% (HPLC), powder

  • 550-24-3

  • E1406-10MG

  • 954.72CNY

  • Detail
  • Sigma

  • (E1406)  Embelin  ≥98% (HPLC), powder

  • 550-24-3

  • E1406-50MG

  • 3,442.14CNY

  • Detail

550-24-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name embelin

1.2 Other means of identification

Product number -
Other names 2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:550-24-3 SDS

550-24-3Synthetic route

2,5-bis-methylamino-3-undecyl-[1,4]benzoquinone
775350-90-8

2,5-bis-methylamino-3-undecyl-[1,4]benzoquinone

embelin
550-24-3

embelin

Conditions
ConditionsYield
With sulfuric acid; acetic acid
dilauryl peroxide
105-74-8

dilauryl peroxide

2.5-dihydroxy-benzoquinone-(1.4)

2.5-dihydroxy-benzoquinone-(1.4)

A

embelin
550-24-3

embelin

B

3.6-dihydroxy-2.5-diundecyl-benzoquinone-(1.4)

3.6-dihydroxy-2.5-diundecyl-benzoquinone-(1.4)

Conditions
ConditionsYield
With acetic acid at 92℃;
3-undecyl-benzene-1,2,4,5-tetraol
850878-20-5

3-undecyl-benzene-1,2,4,5-tetraol

alkali

alkali

air

air

embelin
550-24-3

embelin

2-phenylamino-5-hydroxy-6-undecyl-1,4-naphthoquinone
56923-51-4

2-phenylamino-5-hydroxy-6-undecyl-1,4-naphthoquinone

alcoholic sulfate

alcoholic sulfate

A

embelin
550-24-3

embelin

B

aniline
62-53-3

aniline

n-dodecanoyl chloride
112-16-3

n-dodecanoyl chloride

embelin
550-24-3

embelin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium peroxide; petroleum ether; water / 0 - 10 °C
2: acetic acid / 92 °C
View Scheme
formaldehyd
50-00-0

formaldehyd

embelin
550-24-3

embelin

ethyl vinyl ether
109-92-2

ethyl vinyl ether

2-ethoxy-6-hydroxy-7-undecyl-3,4-dihydro-2H-chromene-5,8-dione
1063976-79-3

2-ethoxy-6-hydroxy-7-undecyl-3,4-dihydro-2H-chromene-5,8-dione

Conditions
ConditionsYield
In ethanol at 150℃; for 0.333333h; microwave irradiation;100%
embelin
550-24-3

embelin

5-chloro-2-((3-(3-nitrophenyl)prop-2-yn-1-yl)oxy)benzaldehyde

5-chloro-2-((3-(3-nitrophenyl)prop-2-yn-1-yl)oxy)benzaldehyde

11-chloro-2-hydroxy-6-(3-nitrophenyl)-3-undecylchromeno[3,4-c]chromene-1,4(7H,12bH)dione

11-chloro-2-hydroxy-6-(3-nitrophenyl)-3-undecylchromeno[3,4-c]chromene-1,4(7H,12bH)dione

Conditions
ConditionsYield
With ethylenediaminediacetic acid In 1,2-dichloro-ethane at 120℃; for 0.166667h; Microwave irradiation; Sealed tube; regioselective reaction;100%
embelin
550-24-3

embelin

C17H28B2O8

C17H28B2O8

Conditions
ConditionsYield
With borax In ethanol for 1h; Heating;98%
embelin
550-24-3

embelin

3-amino-cyclohex-2-enone
5220-49-5

3-amino-cyclohex-2-enone

3-Fluorobenzaldehyde
456-48-4

3-Fluorobenzaldehyde

9-(3-fluorophenyl)-2-hydroxy-3-undecyl-6,7,9,10-tetrahydro-5H-acridine-1,4,8-trione
1448168-14-6

9-(3-fluorophenyl)-2-hydroxy-3-undecyl-6,7,9,10-tetrahydro-5H-acridine-1,4,8-trione

Conditions
ConditionsYield
In ethanol at 150℃; for 0.25h; Microwave irradiation;98%
embelin
550-24-3

embelin

5-chloro-2-((3-(3-methoxyphenyl)prop-2-yn-1-yl)oxy)benzaldehyde

5-chloro-2-((3-(3-methoxyphenyl)prop-2-yn-1-yl)oxy)benzaldehyde

11-chloro-2-hydroxy-6-(3-methoxyphenyl)-3-undecylchromeno-[3,4-c]chromene-1,4(7H,12bH)dione

11-chloro-2-hydroxy-6-(3-methoxyphenyl)-3-undecylchromeno-[3,4-c]chromene-1,4(7H,12bH)dione

Conditions
ConditionsYield
With ethylenediaminediacetic acid In 1,2-dichloro-ethane at 120℃; for 0.166667h; Microwave irradiation; Sealed tube; regioselective reaction;98%
embelin
550-24-3

embelin

C11H11N3O2S2
627061-10-3

C11H11N3O2S2

7-hydroxy-2-(p-methoxyphenacylsulfanyl)-6-undecyl[1,3,4]thiadiazolo[3,2-a]benzimidazole-5,8-dione
1220687-98-8

7-hydroxy-2-(p-methoxyphenacylsulfanyl)-6-undecyl[1,3,4]thiadiazolo[3,2-a]benzimidazole-5,8-dione

Conditions
ConditionsYield
With acetic acid for 4h; Reflux; regioselective reaction;97%
2,6-dimethyl-5-hepten-1-al
106-72-9

2,6-dimethyl-5-hepten-1-al

embelin
550-24-3

embelin

(±)-8-hydroxy-1,4,4-trimethyl-7-undecyl-1,2,3,3a,4,9b-hexahydrocyclopenta[c]chromene-6,9-dione

(±)-8-hydroxy-1,4,4-trimethyl-7-undecyl-1,2,3,3a,4,9b-hexahydrocyclopenta[c]chromene-6,9-dione

Conditions
ConditionsYield
With ethylenediaminediacetic acid In dichloromethane at 20℃; regioselective reaction;97%
embelin
550-24-3

embelin

2-((5-amino-1,3,4-thiadiazol-2-yl)thio)-1-phenylethanone
300726-25-4

2-((5-amino-1,3,4-thiadiazol-2-yl)thio)-1-phenylethanone

7-hydroxy-2-(phenacylsulfanyl)-6-undecyl[1,3,4]thiadiazolo[3,2-a]benzimidazole-5,8-dione
1220687-95-5

7-hydroxy-2-(phenacylsulfanyl)-6-undecyl[1,3,4]thiadiazolo[3,2-a]benzimidazole-5,8-dione

Conditions
ConditionsYield
With acetic acid for 4h; Reflux; regioselective reaction;96%
embelin
550-24-3

embelin

benzaldehyde
100-52-7

benzaldehyde

3-amino-cyclohex-2-enone
5220-49-5

3-amino-cyclohex-2-enone

9-phenyl-2-hydroxy-3-undecyl-6,7,9,10-tetrahydro-5H-acridine-1,4,8-trione
1448168-18-0

9-phenyl-2-hydroxy-3-undecyl-6,7,9,10-tetrahydro-5H-acridine-1,4,8-trione

Conditions
ConditionsYield
In ethanol at 150℃; for 0.25h;96%
2-amino-5-methylthio-1,3,4-thiadiazole
5319-77-7

2-amino-5-methylthio-1,3,4-thiadiazole

embelin
550-24-3

embelin

7-hydroxy-2-(methylsulfanyl)-6-undecyl[1,3,4]thiadiazolo[3,2-a]benzimidazole-5,8-dione
1220687-86-4

7-hydroxy-2-(methylsulfanyl)-6-undecyl[1,3,4]thiadiazolo[3,2-a]benzimidazole-5,8-dione

Conditions
ConditionsYield
With acetic acid for 4h; Reflux; regioselective reaction;95%
5-bromo-pyridine-2,3-diamine
38875-53-5

5-bromo-pyridine-2,3-diamine

embelin
550-24-3

embelin

3-bromo-6-undecylpyrido[2,3-b]quinoxaline-7,8-diol

3-bromo-6-undecylpyrido[2,3-b]quinoxaline-7,8-diol

Conditions
ConditionsYield
In acetic acid for 1h; Reflux;95%
embelin
550-24-3

embelin

3-nitro-aniline
99-09-2

3-nitro-aniline

5-(3-nitrophenylamino)-2-hydroxy-3-undecyl-1,4-benzoquinone
1346520-35-1

5-(3-nitrophenylamino)-2-hydroxy-3-undecyl-1,4-benzoquinone

Conditions
ConditionsYield
Reflux; regioselective reaction;94.44%
2-amino-5-benzylthio-1,3,4-thiadiazole
25660-71-3

2-amino-5-benzylthio-1,3,4-thiadiazole

embelin
550-24-3

embelin

7-hydroxy-2-(benzylsulfanyl)-6-undecyl[1,3,4]thiadiazolo[3,2-a]benzimidazole-5,8-dione
1220687-92-2

7-hydroxy-2-(benzylsulfanyl)-6-undecyl[1,3,4]thiadiazolo[3,2-a]benzimidazole-5,8-dione

Conditions
ConditionsYield
With acetic acid for 4h; Reflux; regioselective reaction;94%
embelin
550-24-3

embelin

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

malononitrile
109-77-3

malononitrile

2-amino-6-hydroxy-4-(4-nitrophenyl)-5,8-dioxo-7-undecyl-5,8-dihydro-4H-chromene-3-carbonitrile

2-amino-6-hydroxy-4-(4-nitrophenyl)-5,8-dioxo-7-undecyl-5,8-dihydro-4H-chromene-3-carbonitrile

Conditions
ConditionsYield
With triethylamine In ethanol for 1.5h; Reflux;94%
embelin
550-24-3

embelin

C11H11N3OS2
627061-09-0

C11H11N3OS2

7-hydroxy-2-(p-methylphenacylsulfanyl)-6-undecyl[1,3,4]thiadiazolo[3,2-a]benzimidazole-5,8-dione
1220687-97-7

7-hydroxy-2-(p-methylphenacylsulfanyl)-6-undecyl[1,3,4]thiadiazolo[3,2-a]benzimidazole-5,8-dione

Conditions
ConditionsYield
With acetic acid for 4h; Reflux; regioselective reaction;93%
Cyanothioacetamide
7357-70-2

Cyanothioacetamide

embelin
550-24-3

embelin

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

2-amino-5,8-dihydro-6-hydroxy-4-(4-hydroxyphenyl)-5,8-dioxo-7-undecyl-4H-chromene-3-carbothioamide
1374881-63-6

2-amino-5,8-dihydro-6-hydroxy-4-(4-hydroxyphenyl)-5,8-dioxo-7-undecyl-4H-chromene-3-carbothioamide

Conditions
ConditionsYield
With zinc(II) chloride In ethanol at 20℃; for 5h;93%
heptanal
111-71-7

heptanal

embelin
550-24-3

embelin

3-amino-cyclohex-2-enone
5220-49-5

3-amino-cyclohex-2-enone

9-hexyl-2-hydroxy-3-undecyl-6,7-dihydroacridine-1,4,8-(5H,8H,10H)-trione
1448168-21-5

9-hexyl-2-hydroxy-3-undecyl-6,7-dihydroacridine-1,4,8-(5H,8H,10H)-trione

Conditions
ConditionsYield
In ethanol at 150℃; for 0.25h; Microwave irradiation;93%
embelin
550-24-3

embelin

5-chloro-2-((3-(4-methoxyphenyl)prop-2-yn-1-yl)oxy)benzaldehyde

5-chloro-2-((3-(4-methoxyphenyl)prop-2-yn-1-yl)oxy)benzaldehyde

11-chloro-2-hydroxy-6-(4-methoxyphenyl)-3-undecylchromeno-[3,4-c]chromene-1,4(7H,12bH)dione

11-chloro-2-hydroxy-6-(4-methoxyphenyl)-3-undecylchromeno-[3,4-c]chromene-1,4(7H,12bH)dione

Conditions
ConditionsYield
With ethylenediaminediacetic acid In 1,2-dichloro-ethane at 120℃; for 0.166667h; Catalytic behavior; Temperature; Reagent/catalyst; Solvent; Microwave irradiation; Sealed tube; regioselective reaction;93%
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

embelin
550-24-3

embelin

Di-tert-butyl acetylenedicarboxylate
66086-33-7

Di-tert-butyl acetylenedicarboxylate

di-tert-butyl 2-(cyclohexylamino)-5,8-dihydro-6-hydroxy-5,8-dioxo-7-undecyl-4H-chromene-3,4-dicarboxylate

di-tert-butyl 2-(cyclohexylamino)-5,8-dihydro-6-hydroxy-5,8-dioxo-7-undecyl-4H-chromene-3,4-dicarboxylate

Conditions
ConditionsYield
In acetonitrile at 20℃; for 24h;93%
embelin
550-24-3

embelin

benzo[1,2,5]thiadiazole-4,5-diamine
1711-66-6

benzo[1,2,5]thiadiazole-4,5-diamine

10-undecyl-[1,2,5]thiadiazolo[3,4-a]phenazine-8,9-diol

10-undecyl-[1,2,5]thiadiazolo[3,4-a]phenazine-8,9-diol

Conditions
ConditionsYield
In acetic acid for 1h; Reflux;93%
5-[(prop-2-en-1-yl)sulfanyl]-1,3,4-thiadiazol-2-amine
30062-44-3

5-[(prop-2-en-1-yl)sulfanyl]-1,3,4-thiadiazol-2-amine

embelin
550-24-3

embelin

7-hydroxy-2-(allylsulfanyl)-6-undecyl[1,3,4]thiadiazolo[3,2-a]benzimidazole-5,8-dione
1220687-90-0

7-hydroxy-2-(allylsulfanyl)-6-undecyl[1,3,4]thiadiazolo[3,2-a]benzimidazole-5,8-dione

Conditions
ConditionsYield
With acetic acid for 4h; Reflux; regioselective reaction;92%
embelin
550-24-3

embelin

C10H8BrN3OS2
350478-46-5

C10H8BrN3OS2

7-hydroxy-2-(p-bromophenacylsulfanyl)-6-undecyl[1,3,4]thiadiazolo[3,2-a]benzimidazole-5,8-dione
1220688-00-5

7-hydroxy-2-(p-bromophenacylsulfanyl)-6-undecyl[1,3,4]thiadiazolo[3,2-a]benzimidazole-5,8-dione

Conditions
ConditionsYield
With acetic acid for 4h; Reflux; regioselective reaction;92%
Cyanothioacetamide
7357-70-2

Cyanothioacetamide

embelin
550-24-3

embelin

2-hydroxynaphthalene-1-carbaldehyde
708-06-5

2-hydroxynaphthalene-1-carbaldehyde

2-amino-5,8-dihydro-6-hydroxy-4-(2-hydroxynaphthalen-1-yl)-5,8-dioxo-7-undecyl-4H-chromene-3-carbothioamide
1374881-65-8

2-amino-5,8-dihydro-6-hydroxy-4-(2-hydroxynaphthalen-1-yl)-5,8-dioxo-7-undecyl-4H-chromene-3-carbothioamide

Conditions
ConditionsYield
With zinc(II) chloride In ethanol at 20℃; for 5h;92%
embelin
550-24-3

embelin

2-(3-methylbut-2-enyloxy)naphthalene-1-carbaldehyde
58758-47-7

2-(3-methylbut-2-enyloxy)naphthalene-1-carbaldehyde

C33H40O5

C33H40O5

Conditions
ConditionsYield
With ethylenediaminediacetic acid In ethanol at 20℃; regioselective reaction;92%
embelin
550-24-3

embelin

4-methoxy-2-((3-phenylprop-2-yn-1-yl)oxy)benzaldehyde

4-methoxy-2-((3-phenylprop-2-yn-1-yl)oxy)benzaldehyde

2-hydroxy-10-methoxy-6-phenyl-3-undecylchromeno[3,4-c]-chromene-1,4(7H,12bH)dione

2-hydroxy-10-methoxy-6-phenyl-3-undecylchromeno[3,4-c]-chromene-1,4(7H,12bH)dione

Conditions
ConditionsYield
With ethylenediaminediacetic acid In 1,2-dichloro-ethane at 120℃; for 0.166667h; Microwave irradiation; Sealed tube; regioselective reaction;92%
embelin
550-24-3

embelin

2,6-dimethylphenyl isonitrile
119072-54-7, 2769-71-3

2,6-dimethylphenyl isonitrile

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

dimethyl 2-(2,6-dimethylphenylamino)-5,8-dihydro-6-hydroxy-5,8-dioxo-7-undecyl-4H-chromene-3,4-dicarboxylate

dimethyl 2-(2,6-dimethylphenylamino)-5,8-dihydro-6-hydroxy-5,8-dioxo-7-undecyl-4H-chromene-3,4-dicarboxylate

Conditions
ConditionsYield
In acetonitrile at 20℃; for 24h;92%
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

embelin
550-24-3

embelin

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

diethyl 2-(cyclohexylamino)-5,8-dihydro-6-hydroxy-5,8-dioxo-7-undecyl-4H-chromene-3,4-dicarboxylate

diethyl 2-(cyclohexylamino)-5,8-dihydro-6-hydroxy-5,8-dioxo-7-undecyl-4H-chromene-3,4-dicarboxylate

Conditions
ConditionsYield
In acetonitrile at 20℃; for 24h;92%
piperonal
120-57-0

piperonal

embelin
550-24-3

embelin

phenylacetonitrile
140-29-4

phenylacetonitrile

3-(benzo[d][1,3]dioxol-5-yl)-2-(benzylamino)-5-hydroxy-6-undecylbenzofuran-4,7-dione

3-(benzo[d][1,3]dioxol-5-yl)-2-(benzylamino)-5-hydroxy-6-undecylbenzofuran-4,7-dione

Conditions
ConditionsYield
With ethylenediaminediacetic acid In 1,2-dichloro-ethane at 180℃; for 0.25h; Knoevenagel Condensation; Irradiation;92%
embelin
550-24-3

embelin

p-toluidine
106-49-0

p-toluidine

5-(p-tolylamino)-2-hydroxy-3-undecyl-1,4-benzoquinone
1346520-42-0

5-(p-tolylamino)-2-hydroxy-3-undecyl-1,4-benzoquinone

Conditions
ConditionsYield
Reflux; regioselective reaction;91.38%
embelin
550-24-3

embelin

sulfanilamide
63-74-1

sulfanilamide

5-(4-sulfonylaminephenylamino)-2-hydroxy-3-undecyl-1,4-benzoquinone
56923-64-9

5-(4-sulfonylaminephenylamino)-2-hydroxy-3-undecyl-1,4-benzoquinone

Conditions
ConditionsYield
Reflux; regioselective reaction;91.29%
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