Isocurcumenol

CAS# 24063-71-6

Isocurcumenol

2D Structure

Catalog No. BCN3526----Order now to get a substantial discount!

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Isocurcumenol: 5mg $40 In Stock
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Quality Control of Isocurcumenol

3D structure

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Isocurcumenol

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Chemical Properties of Isocurcumenol

Cas No. 24063-71-6 SDF Download SDF
PubChem ID 10399139 Appearance Powder
Formula C15H22O2 M.Wt 234.3
Type of Compound Sesquiterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CC1CCC2C13CC(=C(C)C)C(O3)(CC2=C)O
Standard InChIKey DEBDFZGNZTYPMF-NZBPQXDJSA-N
Standard InChI InChI=1S/C15H22O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h11-12,16H,3,5-8H2,1-2,4H3/t11-,12-,14-,15+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Isocurcumenol

The rhizome of Curcuma wenyujin Y.H.Chen et C.Ling

Biological Activity of Isocurcumenol

DescriptionIsocurcumenol inhibits 5α-reductase which converts testosterone to dihydrotestosterone (DHT).
Targets5α-Reductase
In vivo

Anti-androgenic effect of sesquiterpenes isolated from the rhizomes of Curcuma aeruginosa Roxb.[Pubmed: 22465508]

Fitoterapia. 2012 Jul;83(5):864-71.


METHODS AND RESULTS:
Six sesquiterpenes: germacrone (1), zederone (2), dehydrocurdione (3), curcumenol (4), zedoarondiol (5) and Isocurcumenol (6) were isolated from rhizomes of Curcuma aeruginosa Roxb. (Zingiberaceae). They inhibited 5α-reductase which converts testosterone to dihydrotestosterone (DHT). Germacrone (1) was the most potent (IC(50)=0.42±0.05 mg/mL). Compound 1 was anti-androgenic in LNCaP cells when proliferation was testosterone-induced. The growth of flank gland of male Syrian hamsters is dependent on circulating androgen and when maintained with testosterone, 1 (3, 30, 100μg) inhibited growth but was ineffective against DHT. The similar activity profile was observed on the 5α-reductase inhibitor, finasteride (100 μg) treatment group. The androgen receptor binding assay showed that 1 did not bind to the androgen receptor.
CONCLUSIONS:
In conclusion, 1 showed anti-androgenic effect on in vitro and in vivo assays. One of the possible mechanisms was inhibition 5α-reductase activity. Thus, 1 is a potential lead compound for treatment of androgen-dependent disorders.

Protocol of Isocurcumenol

Structure Identification
Nat Prod Res. 2014;28(20):1680-4.

Comparative study on the chemical constituents of essential oils from different organs of the Sicilian Kundmannia (Kundmannia sicula L.) DC. (Apiaceae) growing spontaneously in Tunisia.[Pubmed: 25022439]

Essential oils from odorous and volatile compounds possessing several therapeutic benefits are considered of a paramount importance in everyday human life.
METHODS AND RESULTS:
This study deals with a comparative study of essential oils from different parts of an aromatic plant Kundmannia sicula (L.) DC. (Apiaceae) growing in Tunisia. The hydro-distilled essential oils of the leaves and inflorescences with mature seeds (IMS) of K. sicula were analysed for the first time by gas chromatography equipped with flame ionisation detector and gas chromatography coupled with mass spectrometry. Fifty leaves and 47 IMS constituents were identified, accounting for 97.9% and 98.2% of the total oil, respectively.
CONCLUSIONS:
The major compounds identified from the leaves and IMS oils were Isocurcumenol (9.9-10.1%), hexadecanoic acid (9.5-10.9%), spathulenol (6.9-3.4%), 10-epi-γ-eudesmol (6.3-5.5%), α-cubebene (5.9-6.1%) and trans-dihydro occidentalol (52-6.6%). The essential oil consists mainly of oxygenated monoterpenes (50.7-53.2%).

Isocurcumenol Dilution Calculator

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Isocurcumenol Molarity Calculator

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Preparing Stock Solutions of Isocurcumenol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.268 mL 21.3402 mL 42.6803 mL 85.3606 mL 106.7008 mL
5 mM 0.8536 mL 4.268 mL 8.5361 mL 17.0721 mL 21.3402 mL
10 mM 0.4268 mL 2.134 mL 4.268 mL 8.5361 mL 10.6701 mL
50 mM 0.0854 mL 0.4268 mL 0.8536 mL 1.7072 mL 2.134 mL
100 mM 0.0427 mL 0.2134 mL 0.4268 mL 0.8536 mL 1.067 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Isocurcumenol

Anti-androgenic effect of sesquiterpenes isolated from the rhizomes of Curcuma aeruginosa Roxb.[Pubmed:22465508]

Fitoterapia. 2012 Jul;83(5):864-71.

Six sesquiterpenes: germacrone (1), zederone (2), dehydrocurdione (3), curcumenol (4), zedoarondiol (5) and Isocurcumenol (6) were isolated from rhizomes of Curcuma aeruginosa Roxb. (Zingiberaceae). They inhibited 5alpha-reductase which converts testosterone to dihydrotestosterone (DHT). Germacrone (1) was the most potent (IC(50)=0.42+/-0.05 mg/mL). Compound 1 was anti-androgenic in LNCaP cells when proliferation was testosterone-induced. The growth of flank gland of male Syrian hamsters is dependent on circulating androgen and when maintained with testosterone, 1 (3, 30, 100mug) inhibited growth but was ineffective against DHT. The similar activity profile was observed on the 5alpha-reductase inhibitor, finasteride (100 mug) treatment group. The androgen receptor binding assay showed that 1 did not bind to the androgen receptor. In conclusion, 1 showed anti-androgenic effect on in vitro and in vivo assays. One of the possible mechanisms was inhibition 5alpha-reductase activity. Thus, 1 is a potential lead compound for treatment of androgen-dependent disorders.

Comparative study on the chemical constituents of essential oils from different organs of the Sicilian Kundmannia (Kundmannia sicula L.) DC. (Apiaceae) growing spontaneously in Tunisia.[Pubmed:25022439]

Nat Prod Res. 2014;28(20):1680-4.

Essential oils from odorous and volatile compounds possessing several therapeutic benefits are considered of a paramount importance in everyday human life. This study deals with a comparative study of essential oils from different parts of an aromatic plant Kundmannia sicula (L.) DC. (Apiaceae) growing in Tunisia. The hydro-distilled essential oils of the leaves and inflorescences with mature seeds (IMS) of K. sicula were analysed for the first time by gas chromatography equipped with flame ionisation detector and gas chromatography coupled with mass spectrometry. Fifty leaves and 47 IMS constituents were identified, accounting for 97.9% and 98.2% of the total oil, respectively. The major compounds identified from the leaves and IMS oils were Isocurcumenol (9.9-10.1%), hexadecanoic acid (9.5-10.9%), spathulenol (6.9-3.4%), 10-epi-gamma-eudesmol (6.3-5.5%), alpha-cubebene (5.9-6.1%) and trans-dihydro occidentalol (52-6.6%). The essential oil consists mainly of oxygenated monoterpenes (50.7-53.2%).

Description

Isocurcumenol, an estrogen receptor alpha (ERα) inhibitor isolated from Curcuma zedoaria Rhizomes, possesses anti-tumor acticity, with IC50 values of 99.1µg/mL and 178.2 µg/mL in DLA and KB cells, respectively.

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