Demethoxycurcumin | CAS# 22608-11-3 | Neuroprotective Agent

MedKoo Cat#: 564540 | Name: Demethoxycurcumin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Demethoxycurcumin is a natural neuroprotective agent, and a metabolite of curcumin.

Chemical Structure

Demethoxycurcumin

CAS#22608-11-3

Theoretical Analysis

MedKoo Cat#: 564540

Name: Demethoxycurcumin

CAS#: 22608-11-3

Chemical Formula: C20H18O5

Exact Mass: 338.1154

Molecular Weight: 338.36

Elemental Analysis: C, 71.00; H, 5.36; O, 23.64

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
250mg	USD 1,250.00	2 Weeks

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Synonym

Monodemethoxycurcumin; Demethoxycurcumin; curcumin II; desmethoxycurcumin; BHCFM; Demethoxy Curcumin; DMC

IUPAC/Chemical Name

(1E,6E)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione

InChi Key

HJTVQHVGMGKONQ-LUZURFALSA-N

InChi Code

InChI=1S/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3/b9-4+,10-5+

SMILES Code

O=C(CC(/C=C/C1=CC=C(O)C=C1)=O)/C=C/C2=CC=C(O)C(OC)=C2

Appearance

Solid powder

Purity

>98% (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

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Demethoxycurcumin(Curcumin II) is a major active curcuminoid that possess anti-inflammatory properties and exerts cytotoxic effects in human cancer cells via induction of apoptosis.

In vitro activity:

It was examined whether DMC can induce the activation of three major MAPKs including extracellular signal-regulated kinase (ERK), c-Jun N-terminal kinase (JNK), and p38. As shown in Figure 5A,B, DMC significantly activated JNK1/2 and p38 MAPK, but not ERK1/2, in concentration-dependent manners. To further determine the role of JNK1/2 and p38 MAPK activation in DMCinduced HO-1 upregulation and cell apoptosis, 1 h of pretreatment of 10 μM SB203580 (a p38 inhibitor) or 1 μM JNK-in-8 (a JNK inhibitor) with HSC-3 cells was followed by 50 μM DMC treatment for another 24 h, and then cells were subjected to Western blotting analysis (Figure 5C). The results revealed that only the inhibition of p38 MAPK in HSC-3 cells considerably reversed DMCinduced HO-1 expression and caspase-8/-9/-3 activation (Figure 5D). A similar phenomenon was also observed in SCC-9 cells (Figure S2). Overall, these results suggest that DMC induces caspase-mediated cell apoptosis through activating the p38 MAPK-HO-1 signaling cascade in OSCC cells. Reference: Cancers (Basel). 2020 Mar 16;12(3):703. https://pubmed.ncbi.nlm.nih.gov/32188144/

In vivo activity:

In the present study, the effects of DMC on GBM8401 cells were investigated in vivo. Mice were randomly divided into three groups: Group I was treated with 110 µL phosphate-buffered solution (PBS) containing 0.1% dimethyl sulfoxide, Group II with 30 mg/kg of DMC, and Group III with 60 mg/kg of DMC. DMC significantly decreased the tumor volumes, and 60 mg/kg treatment showed a higher decrease in tumor volumes than that of 30 mg/kg, However, DMC did not affect the body weights. DMC at both doses decreased the total photon flux and 60 mg/kg treatment of DMC has low total photon flux than that of 30 mg/kg. The tumor volumes and weights in 60 mg/kg treatment of DMC were lower than that of 30 mg/kg. DMC treatment led to lightly staining with anti-Bcl-2 and -XIAP and 60 mg/kg treatment of DMC has lighter staining with anti-Bcl-2 and -XIAP than that of 30 mg/kg. The higher dose (60 mg/kg) of DMC has higher signals of cleaved-caspase-3 than that of the lower dose (30 mg/kg). Reference: Int J Mol Sci. 2021 May 23;22(11):5503. https://pubmed.ncbi.nlm.nih.gov/34071132/

	Solvent	mg/mL	mM
Solubility
	DMSO	59.0	174.37

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 338.36 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. Chien MH, Yang WE, Yang YC, Ku CC, Lee WJ, Tsai MY, Lin CW, Yang SF. Dual Targeting of the p38 MAPK-HO-1 Axis and cIAP1/XIAP by Demethoxycurcumin Triggers Caspase-Mediated Apoptotic Cell Death in Oral Squamous Cell Carcinoma Cells. Cancers (Basel). 2020 Mar 16;12(3):703. doi: 10.3390/cancers12030703. PMID: 32188144; PMCID: PMC7140023. 2. Chen Y, Hong C, Chen X, Qin Z. Demethoxycurcumin increases the sensitivity of cisplatin-resistant non-small lung cancer cells to cisplatin and induces apoptosis by activating the caspase signaling pathway. Oncol Lett. 2020 Nov;20(5):209. doi: 10.3892/ol.2020.12072. Epub 2020 Sep 8. PMID: 32963615; PMCID: PMC7491090. 3. Huang YP, Ma YS, Kuo CL, Liao CL, Chen PY, Peng SF, Hsu FT, Lai KC. Demethoxycurcumin Suppresses Human Brain Glioblastoma Multiforme GBM 8401 Cell Xenograft Tumor in Nude Mice In Vivo. Int J Mol Sci. 2021 May 23;22(11):5503. doi: 10.3390/ijms22115503. PMID: 34071132; PMCID: PMC8197162. 4. Chueh FS, Lien JC, Chou YC, Huang WW, Huang YP, Huang JY, Kuo JY, Huang WN, Sheng SY, Tung HY, Chen HY, Peng SF. Demethoxycurcumin Inhibits In Vivo Growth of Xenograft Tumors of Human Cervical Cancer Cells. In Vivo. 2020 SepOct;34(5):2469-2474. doi: 10.21873/invivo.12062. PMID: 32871774; PMCID: PMC7652493.

In vitro protocol:

In vivo protocol:

1. Huang YP, Ma YS, Kuo CL, Liao CL, Chen PY, Peng SF, Hsu FT, Lai KC. Demethoxycurcumin Suppresses Human Brain Glioblastoma Multiforme GBM 8401 Cell Xenograft Tumor in Nude Mice In Vivo. Int J Mol Sci. 2021 May 23;22(11):5503. doi: 10.3390/ijms22115503. PMID: 34071132; PMCID: PMC8197162. 2. Chueh FS, Lien JC, Chou YC, Huang WW, Huang YP, Huang JY, Kuo JY, Huang WN, Sheng SY, Tung HY, Chen HY, Peng SF. Demethoxycurcumin Inhibits In Vivo Growth of Xenograft Tumors of Human Cervical Cancer Cells. In Vivo. 2020 SepOct;34(5):2469-2474. doi: 10.21873/invivo.12062. PMID: 32871774; PMCID: PMC7652493.

1: Kotha RR, Luthria DL. Curcumin: Biological, Pharmaceutical, Nutraceutical, and Analytical Aspects. Molecules. 2019 Aug 13;24(16):2930. doi: 10.3390/molecules24162930. PMID: 31412624; PMCID: PMC6720683. 2: Hatamipour M, Ramezani M, Tabassi SAS, Johnston TP, Sahebkar A. Demethoxycurcumin: A naturally occurring curcumin analogue for treating non- cancerous diseases. J Cell Physiol. 2019 Nov;234(11):19320-19330. doi: 10.1002/jcp.28626. Epub 2019 Apr 4. PMID: 31344992. 3: Lestari ML, Indrayanto G. Curcumin. Profiles Drug Subst Excip Relat Methodol. 2014;39:113-204. doi: 10.1016/B978-0-12-800173-8.00003-9. PMID: 24794906. 4: Hatamipour M, Ramezani M, Tabassi SAS, Johnston TP, Ramezani M, Sahebkar A. Demethoxycurcumin: A naturally occurring curcumin analogue with antitumor properties. J Cell Physiol. 2018 Dec;233(12):9247-9260. doi: 10.1002/jcp.27029. Epub 2018 Aug 4. PMID: 30076727. 5: Ramkumar M, Rajasankar S, Swaminathan Johnson WM, Prabu K, Venkatesh Gobi V. Demethoxycurcumin ameliorates rotenone-induced toxicity in rats. Front Biosci (Elite Ed). 2019 Jan 1;11(1):1-11. doi: 10.2741/E841. PMID: 30468633. 6: Tang J, Peng H, Xu F, Luo P, Liu D, Chen L. Demethoxycurcumin represses cervical cancer growth through PPARγ-regulated proliferation and apoptosis. Acta Biochim Biophys Sin (Shanghai). 2023 Feb 28;55(8):1331-1333. doi: 10.3724/abbs.2023077. PMID: 37140232; PMCID: PMC10448040. 7: Shi L, Sun G, Zhang Y. Demethoxycurcumin analogue DMC-BH exhibits potent anticancer effects on orthotopic glioblastomas. Aging (Albany NY). 2020 Nov 18;12(23):23795-23807. doi: 10.18632/aging.103981. Epub 2020 Nov 18. PMID: 33221748; PMCID: PMC7762498. 8: Lu B, Chen X, Chen H, Li Q, Li H, Xu Y, Li Y, Shen X, Jiang R. Demethoxycurcumin mitigates inflammatory responses in lumbar disc herniation via MAPK and NF-κB pathways in vivo and in vitro. Int Immunopharmacol. 2022 Jul;108:108914. doi: 10.1016/j.intimp.2022.108914. Epub 2022 Jun 4. PMID: 35729841. 9: Du Z, Sha X. Demethoxycurcumin inhibited human epithelia ovarian cancer cells' growth via up-regulating miR-551a. Tumour Biol. 2017 Mar;39(3):1010428317694302. doi: 10.1177/1010428317694302. PMID: 28345465. 10: Chainani-Wu N. Safety and anti-inflammatory activity of curcumin: a component of tumeric (Curcuma longa). J Altern Complement Med. 2003 Feb;9(1):161-8. doi: 10.1089/107555303321223035. PMID: 12676044. 11: Hashem S, Nisar S, Sageena G, Macha MA, Yadav SK, Krishnankutty R, Uddin S, Haris M, Bhat AA. Therapeutic Effects of Curcumol in Several Diseases; An Overview. Nutr Cancer. 2021;73(2):181-195. doi: 10.1080/01635581.2020.1749676. Epub 2020 Apr 14. PMID: 32285707. 12: Teng YN, Hsieh YW, Hung CC, Lin HY. Demethoxycurcumin modulates human P-glycoprotein function via uncompetitive inhibition of ATPase hydrolysis activity. J Agric Food Chem. 2015 Jan 28;63(3):847-55. doi: 10.1021/jf5042307. Epub 2015 Jan 16. PMID: 25594233. 13: Chueh FS, Lien JC, Chou YC, Huang WW, Huang YP, Huang JY, Kuo JY, Huang WN, Sheng SY, Tung HY, Chen HY, Peng SF. Demethoxycurcumin Inhibits In Vivo Growth of Xenograft Tumors of Human Cervical Cancer Cells. In Vivo. 2020 Sep- Oct;34(5):2469-2474. doi: 10.21873/invivo.12062. PMID: 32871774; PMCID: PMC7652493. 14: Lee GJ, Lim H, Seo JY, Kang KR, Kim DK, You JS, Oh JS, Seo YS, Kim JS. Demethoxycurcumin induces apoptosis via inhibition of NF-κB pathway in FaDu human head and neck squamous cell carcinoma. Transl Cancer Res. 2022 May;11(5):1064-1075. doi: 10.21037/tcr-21-2410. PMID: 35706794; PMCID: PMC9189212. 15: Shi L, Sun G, Zhu H. Demethoxycurcumin analogue DMC-BH inhibits orthotopic growth of glioma stem cells by targeting JNK/ERK signaling. Aging (Albany NY). 2020 Jul 24;12(14):14718-14735. doi: 10.18632/aging.103531. Epub 2020 Jul 24. PMID: 32710727; PMCID: PMC7425509. 16: Jäger R, Lowery RP, Calvanese AV, Joy JM, Purpura M, Wilson JM. Comparative absorption of curcumin formulations. Nutr J. 2014 Jan 24;13:11. doi: 10.1186/1475-2891-13-11. PMID: 24461029; PMCID: PMC3918227. 17: Lin YJ, Chen CJ, Hsueh SC, Lee MH, Peng SF, Lu HF, Lu KW, Huang WW, Liu KC, Chen YL, Shih YL, Lien JC. Demethoxycurcumin Promotes Macrophage Cell Population and Phagocytosis in WEHI-3 Cell-generated Leukemia BALB/c Mice In Vivo. In Vivo. 2021 Nov-Dec;35(6):3253-3260. doi: 10.21873/invivo.12620. PMID: 34697156; PMCID: PMC8627730. 18: Huang YP, Ma YS, Kuo CL, Liao CL, Chen PY, Peng SF, Hsu FT, Lai KC. Demethoxycurcumin Suppresses Human Brain Glioblastoma Multiforme GBM 8401 Cell Xenograft Tumor in Nude Mice In Vivo. Int J Mol Sci. 2021 May 23;22(11):5503. doi: 10.3390/ijms22115503. PMID: 34071132; PMCID: PMC8197162. 19: Kao CC, Cheng YC, Yang MH, Cha TL, Sun GH, Ho CT, Lin YC, Wang HK, Wu ST, Way TD. Demethoxycurcumin induces apoptosis in HER2 overexpressing bladder cancer cells through degradation of HER2 and inhibiting the PI3K/Akt pathway. Environ Toxicol. 2021 Nov;36(11):2186-2195. doi: 10.1002/tox.23332. Epub 2021 Jul 22. PMID: 34291863; PMCID: PMC9292507. 20: Li QQ, Kang OH, Kwon DY. Study on Demethoxycurcumin as a Promising Approach to Reverse Methicillin-Resistance of Staphylococcus aureus. Int J Mol Sci. 2021 Apr 6;22(7):3778. doi: 10.3390/ijms22073778. PMID: 33917423; PMCID: PMC8038695.