Synonym
Curcumin; Diferuloylmethane; Turmeric Yellow; curcumin I; C.I. 75300; Natural Yellow 3; NSC32982; UNIIIT942ZTH98.
IUPAC/Chemical Name
(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
InChi Key
VFLDPWHFBUODDF-FCXRPNKRSA-N
InChi Code
InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-12,24-25H,13H2,1-2H3/b7-3+,8-4+
SMILES Code
O=C(CC(/C=C/C1=CC=C(O)C(OC)=C1)=O)/C=C/C2=CC=C(O)C(OC)=C2
Appearance
Orange solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
A 2014 review of human clinical trials found no benefit to 5-8 weeks of curcumin consumption compared to placebo or no treatment for patients with major depressive disorder. A number of trials studying curcumin efficacy and safety revealed poor absorption and low bioavailability. (Source: http://en.wikipedia.org/wiki/Curcumin).
Biological target:
Curcumin (Diferuloylmethane), a natural phenolic compound, is a p300/CREB-binding protein-specific inhibitor of acetyltransferase.
In vitro activity:
In summary, this study found that curcumin can inhibit PA (palmitic acid)-induced oxidative stress, autophagy, and apoptosis. Thus, this study assumes that curcumin indirectly inhibits the PA-induced autophagy via suppressing oxidative stress. To further clarify this hypothesis, this study found that curcumin inhibited H2O2-induced oxidative stress, autophagy, and apoptosis, but curcumin had no obvious effects on AY-22989-induced autophagy. Therefore, curcumin ameliorates PA-induced human Saos-2 cell apoptosis by inhibiting oxidative stress-mediated autophagy.
Reference: Evid Based Complement Alternat Med. 2021; 2021: 5563660. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8018866/
In vivo activity:
As shown in figure 6, the WAT (white adipose tissue) adipocytes were less organized (figure 6a) and the volume of fat cells was significantly larger in DIO group mice compared to those in normal group mice (figure 6c). After curcumin (50 mg kg−1 d−1) treatment, the cell sizes were markedly decreased. The nuclei (blue) and cytoplasm (pink) of adipose cells were squeezed to one side because of the emergence of lipid droplets in the DIO group compared with those in normal BAT (brown adipose tissue) (figure 6b). Moreover, the BAT architecture in obese mice demonstrated a higher number of lipid droplets. Curcumin treatment significantly decreased the fat cell size and attenuated lipid droplet accumulation compared with those in the DIO group (figure 6d). Interestingly, more visible cavity beige fat cells were observed in the curcumin treatment group than in the control group, which indicated that curcumin can inhibit the hypertrophy of white fat cells and promote the transition of white fat cells to brown fat cells.
Reference: R Soc Open Sci. 2021 Mar; 8(3): 200974. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8074937/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
96.5 |
261.96 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
368.38
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Chehardoli B, Nadi M, Khamis Abadi A, Kia A, Shahriary A, Salimian J. Immunomodulatory Effect of Curcumin in the Upregulation of Inflammasome Pathway Genes Induced by Sulfur Mustard Analog: An In-vitro Study. Iran J Allergy Asthma Immunol. 2021 Apr 17;20(2):169-177. PMID: 33904675.
2. Ma B, Guan G, Lv Q, Yang L. Curcumin Ameliorates Palmitic Acid-Induced Saos-2 Cell Apoptosis Via Inhibiting Oxidative Stress and Autophagy. Evid Based Complement Alternat Med. 2021 Mar 26;2021:5563660. doi: 10.1155/2021/5563660. PMID: 33833814; PMCID: PMC8018866.
3. Huang X, Liang C, Yang H, Li X, Deng X, Liang X, Li L, Huang Z, Lu D, Ma Y, Luo Z. Curcumin induces apoptosis and inhibits the growth of adrenocortical carcinoma: Identification of potential candidate genes and pathways by transcriptome analysis. Oncol Lett. 2021 Jun;21(6):476. doi: 10.3892/ol.2021.12737. Epub 2021 Apr 15. PMID: 33907586; PMCID: PMC8063251.
4. Zhao D, Pan Y, Yu N, Bai Y, Ma R, Mo F, Zuo J, Chen B, Jia Q, Zhang D, Liu J, Jiang G, Gao S. Curcumin improves adipocytes browning and mitochondrial function in 3T3-L1 cells and obese rodent model. R Soc Open Sci. 2021 Mar 17;8(3):200974. doi: 10.1098/rsos.200974. PMID: 33959308; PMCID: PMC8074937.
In vitro protocol:
1. Chehardoli B, Nadi M, Khamis Abadi A, Kia A, Shahriary A, Salimian J. Immunomodulatory Effect of Curcumin in the Upregulation of Inflammasome Pathway Genes Induced by Sulfur Mustard Analog: An In-vitro Study. Iran J Allergy Asthma Immunol. 2021 Apr 17;20(2):169-177. PMID: 33904675.
2. Ma B, Guan G, Lv Q, Yang L. Curcumin Ameliorates Palmitic Acid-Induced Saos-2 Cell Apoptosis Via Inhibiting Oxidative Stress and Autophagy. Evid Based Complement Alternat Med. 2021 Mar 26;2021:5563660. doi: 10.1155/2021/5563660. PMID: 33833814; PMCID: PMC8018866.
In vivo protocol:
1. Huang X, Liang C, Yang H, Li X, Deng X, Liang X, Li L, Huang Z, Lu D, Ma Y, Luo Z. Curcumin induces apoptosis and inhibits the growth of adrenocortical carcinoma: Identification of potential candidate genes and pathways by transcriptome analysis. Oncol Lett. 2021 Jun;21(6):476. doi: 10.3892/ol.2021.12737. Epub 2021 Apr 15. PMID: 33907586; PMCID: PMC8063251.
2. Zhao D, Pan Y, Yu N, Bai Y, Ma R, Mo F, Zuo J, Chen B, Jia Q, Zhang D, Liu J, Jiang G, Gao S. Curcumin improves adipocytes browning and mitochondrial function in 3T3-L1 cells and obese rodent model. R Soc Open Sci. 2021 Mar 17;8(3):200974. doi: 10.1098/rsos.200974. PMID: 33959308; PMCID: PMC8074937.
1: Rivera-MancÃa S, Lozada-GarcÃa MC, Pedraza-Chaverri J. Experimental evidence for curcumin and its analogs for management of diabetes mellitus and its associated complications. Eur J Pharmacol. 2015 Mar 10. pii: S0014-2999(15)00164-8. doi: 10.1016/j.ejphar.2015.02.045. [Epub ahead of print] Review. PubMed PMID: 25769841.
2: Ghorbani Z, Hekmatdoost A, Mirmiran P. Anti-hyperglycemic and insulin sensitizer effects of turmeric and its principle constituent curcumin. Int J Endocrinol Metab. 2014 Oct 1;12(4):e18081. doi: 10.5812/ijem.18081. eCollection 2014 Oct. Review. PubMed PMID: 25745485; PubMed Central PMCID: PMC4338652.
3: Vallianou NG, Evangelopoulos A, Schizas N, Kazazis C. Potential anticancer properties and mechanisms of action of curcumin. Anticancer Res. 2015 Feb;35(2):645-51. Review. PubMed PMID: 25667441.
4: Sordillo PP, Helson L. Curcumin and cancer stem cells: curcumin has asymmetrical effects on cancer and normal stem cells. Anticancer Res. 2015 Feb;35(2):599-614. Review. PubMed PMID: 25667437.
5: Shanmugam MK, Rane G, Kanchi MM, Arfuso F, Chinnathambi A, Zayed ME, Alharbi SA, Tan BK, Kumar AP, Sethi G. The multifaceted role of curcumin in cancer prevention and treatment. Molecules. 2015 Feb 5;20(2):2728-69. doi: 10.3390/molecules20022728. Review. PubMed PMID: 25665066.
6: Tuorkey MJ. Curcumin a potent cancer preventive agent: Mechanisms of cancer cell killing. Interv Med Appl Sci. 2014 Dec;6(4):139-46. doi: 10.1556/IMAS.6.2014.4.1. Epub 2014 Dec 22. Review. PubMed PMID: 25598986; PubMed Central PMCID: PMC4274352.
7: Bandyopadhyay D. Farmer to pharmacist: curcumin as an anti-invasive and antimetastatic agent for the treatment of cancer. Front Chem. 2014 Dec 23;2:113. doi: 10.3389/fchem.2014.00113. eCollection 2014. Review. PubMed PMID: 25566531; PubMed Central PMCID: PMC4275038.
8: Renuga Parameswari A, Rajalakshmi G, Kumaradhas P. A combined molecular docking and charge density analysis is a new approach for medicinal research to understand drug-receptor interaction: curcumin-AChE model. Chem Biol Interact. 2015 Jan 5;225:21-31. doi: 10.1016/j.cbi.2014.09.011. Epub 2014 Oct 13. Review. PubMed PMID: 25446495.
9: Maiti P, Manna J, Veleri S, Frautschy S. Molecular chaperone dysfunction in neurodegenerative diseases and effects of curcumin. Biomed Res Int. 2014;2014:495091. doi: 10.1155/2014/495091. Epub 2014 Oct 19. Review. PubMed PMID: 25386560; PubMed Central PMCID: PMC4217372.
10: Rahmani AH, Al Zohairy MA, Aly SM, Khan MA. Curcumin: a potential candidate in prevention of cancer via modulation of molecular pathways. Biomed Res Int. 2014;2014:761608. doi: 10.1155/2014/761608. Epub 2014 Sep 10. Review. PubMed PMID: 25295272; PubMed Central PMCID: PMC4176907.
