Isoprocurcumenol is a guaiac-type sesquiterpene extracted from Curcuma comosa. Isoprocurcumenol activates EGFR signaling. Isoprocurcumenol increases the phosphorylation of ERK and AKT. Isoprocurcumenol promotes the proliferation of keratinocytes.

Physicochemical Properties

Molecular Formula	C15H22O2
Molecular Weight	234.33
Exact Mass	234.161
CAS #	102130-90-5
PubChem CID	14543197
Appearance	White to off-white solid powder
Density	1.1±0.1 g/cm3
Boiling Point	360.3±41.0 °C at 760 mmHg
Melting Point	99.5-100.5 ºC (hexane )
Flash Point	153.7±20.2 °C
Vapour Pressure	0.0±1.8 mmHg at 25°C
Index of Refraction	1.523
LogP	2.59
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Heavy Atom Count	17
Complexity	401
Defined Atom Stereocenter Count	0
InChi Key	ITIGZFMSPAFZAE-UHFFFAOYSA-N
InChi Code	InChI=1S/C15H22O2/c1-9(2)12-8-13-11(5-6-15(13,4)17)10(3)7-14(12)16/h11,13,17H,3,5-8H2,1-2,4H3
Chemical Name	3-hydroxy-3-methyl-8-methylidene-5-propan-2-ylidene-2,3a,4,8a-tetrahydro-1H-azulen-6-one
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	ERK Akt
ln Vitro	Isoprocurcumenol (10 μM, 0-1 h) can enhance the phosphorylation of ERK and AKT [3]. Isoprocurcumenol (0-200 μM, 24 or 48 h) stimulates keratinocyte HaCaT cell growth [3]. Isoprocurcumenol (1 μM, 1 h) stimulates the expression of cell growth and proliferation-related genes, such as c-fos, c-jun, c-myc and egr-1[3], by activating the EGFR signaling pathway. Isoprocurcumenol stimulates cell recovery and wound repair [3].
Cell Assay	Western Blot Analysis[3] Cell Types: HaCaT cells (human keratinocyte cell) Tested Concentrations: 10 μM Incubation Duration: 10, 30, or 60 min Experimental Results: Induced the phosphorylation of ERK and AKT after 10 min and this was sustained for 1 h. Cell Proliferation Assay[3] Cell Types: HaCaT cells (human keratinocyte cell) Tested Concentrations: 0 nM, 1 nM, 10 nM, 100 nM, 1 μM, 10 μM, 25 μM, 50 μM, 100 μM, or 200 μM Incubation Duration: 24 or 48 h Experimental Results: demonstrated a significant increase in the proliferation of cells at most of the Isoprocurcumenol concentrations, starting at 10 nM. RT-PCR[3] Cell Types: HaCaT cells (human keratinocyte cell) Tested Concentrations: 1 μM Incubation Duration: 1 h Experimental Results: Increased the expression of genes related to cell growth and proliferation, such as c-myc, c-jun, c-fos, and egr-1.
References	[1]. Sesquiterpenes from Curcuma comosa. J Nat Med. 2009 Jan;63(1):102-4. [2]. Cytotoxicity and inhibition of leukemic cell proliferation by sesquiterpenes from rhizomes of Mah-Lueang (Curcuma cf. viridiflora Roxb.). Bioorg Med Chem Lett. 2018 Feb 1;28(3):410-414. [3]. Isoprocurcumenol Supports Keratinocyte Growth and Survival through Epidermal Growth Factor Receptor Activation. Int J Mol Sci. 2021 Nov 22;22(22):12579.
Additional Infomation	(1alpha,4beta,5beta)-4-Hydroxy-7(11),10(14)-guaiadien-8-one is a sesquiterpenoid.

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	4.2675 mL	21.3374 mL	42.6749 mL
	5 mM	0.8535 mL	4.2675 mL	8.5350 mL
	10 mM	0.4267 mL	2.1337 mL	4.2675 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.