Carnosol | CAS# 5957-80-2 | anti-cancer

MedKoo Cat#: 412376 | Name: Carnosol

Featured

Description:

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

Carnosol is a phenolic diterpene found in the herbs rosemary and Mountain desert sage. It has been studied in-vitro for anti-cancer effects in various cancer cell types

Chemical Structure

Carnosol

CAS#5957-80-2

Theoretical Analysis

MedKoo Cat#: 412376

Name: Carnosol

CAS#: 5957-80-2

Chemical Formula: C20H26O4

Exact Mass: 330.1831

Molecular Weight: 330.42

Elemental Analysis: C, 72.70; H, 7.93; O, 19.37

Price and Availability

Size	Price	Availability
100mg	USD 350.00	2 Weeks
250mg	USD 650.00	2 Weeks
500mg	USD 950.00	2 Weeks
1g	USD 1,450.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Carnosol; CCRIS7122; CCRIS-7122; CCRIS 7122; HSDB7680; HSDB-7680; HSDB 7680; NSC 39143; NSC39143; NSC-39143

IUPAC/Chemical Name

(4aR,9S,10aS)-5,6-Dihydroxy-7-isopropyl-1,1-dimethyl-2,3,4,9,10,10a-hexahydro-1H-9,4a-(epoxymethano)phenanthren-12-one

InChi Key

XUSYGBPHQBWGAD-PJSUUKDQSA-N

InChi Code

InChI=1S/C20H26O4/c1-10(2)11-8-12-13-9-14-19(3,4)6-5-7-20(14,18(23)24-13)15(12)17(22)16(11)21/h8,10,13-14,21-22H,5-7,9H2,1-4H3/t13-,14-,20+/m0/s1

SMILES Code

O=C1O[C@]2([H])C3=C(C(O)=C(O)C(C(C)C)=C3)[C@@]41CCCC(C)(C)[C@]4([H])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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Carnosol is a potent Ribosomal S6 Kinase (RSK2) inhibitor that could be useful for treating gastric cancer, with an IC50 of ~5.5 μM. Carnosol, a Nrf2 activator, increases the nuclear levels of Nrf2 and can promote the expression of heme oxygenase 1 (HMOX1).

In vitro activity:

Carnosol is an ortho-diphenolic diterpene compound with an abietane carbon skeleton (Figure 1A). To evaluate the effect of carnosol on cytotoxicity, GES1 normal gastric epithelial mucosa cells were treated with this compound. Results showed that carnosol had no cytotoxic effects on GES1 cells (Figure 1B). To determine whether phosphorylated RSK is differentially expressed in normal gastric or gastric cancer cells, Western blot analysis was performed. Results showed that gastric cancer cells highly express phosphorylated RSK compared with normal gastric cells (Supplementary Figure 1). It was next determined whether carnosol could affect gastric cancer cell growth. HGC27, SGC7901 or BGC803 gastric cancer cells were treated with various concentrations of carnosol. Results indicated that carnosol significantly inhibited both anchorage-dependent (Figure 1C) and anchorage-independent (Figure 1D) gastric cancer cell growth in a dose-dependent manner. Reference: Oncotarget. 2018 Feb 6;9(76):34200-34212. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30344937/

In vivo activity:

To examine the anti-tumor activity of carnosol in vivo, patient-derived gastric tumor tissues were injected into the back of the neck of athymic nude mice. Mice were orally administrated carnosol at 100 mg/kg or vehicle 5 times a week over a period of 31 days. Results indicated that carnosol significantly decreased the volume and weight of gastric tumors relative to the vehicle-treated group (Figure 6A, 6B; p < 0.05). Additionally, mice tolerated treatment with carnosol without significant loss of body weight similar to the vehicle-treated group (Supplementary Figure 2A). The effects of carnosol on the Ki-67 tumor proliferation marker was examined by using immunohistochemistry. The expression of Ki-67 was significantly decreased by treatment with carnosol (Figure (Figure6C).6C). Furthermore, to evaluate potential toxic effects of carnosol on tissue morphology, the liver and spleen tissues were stained with hematoxylin and eosin (H&E). Results indicated no obvious morphological changes (Supplementary Figure 2B, 2C). To validate the results of the in vivo PDX model, we investigated the effect of carnosol on RSK2-CREB signaling by Western blot analysis of PDX gastric tumor samples. The phosphorylation of CREB, a direct downstream protein of RSK2, was strongly inhibited in the carnosol-treated group but the expression of total CREB was relatively unchanged (Figure 6D). Reference: Oncotarget. 2018 Feb 6;9(76):34200-34212. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30344937/

	Solvent	mg/mL	mM
Solubility
	DMSO	66.0	199.74

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 330.42 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:

In vitro protocol:

1. Wang L, Zhang Y, Liu K, Chen H, Yang R, Ma X, Kim HG, Bode AM, Kim DJ, Dong Z. Carnosol suppresses patient-derived gastric tumor growth by targeting RSK2. Oncotarget. 2018 Feb 6;9(76):34200-34212. doi: 10.18632/oncotarget.24409. PMID: 30344937; PMCID: PMC6188138. 2. Shi W, Xu G, Zhan X, Gao Y, Wang Z, Fu S, Qin N, Hou X, Ai Y, Wang C, He T, Liu H, Chen Y, Liu Y, Wang J, Niu M, Guo Y, Xiao X, Bai Z. Carnosol inhibits inflammasome activation by directly targeting HSP90 to treat inflammasome-mediated diseases. Cell Death Dis. 2020 Apr 20;11(4):252. doi: 10.1038/s41419-020-2460-x. PMID: 32312957; PMCID: PMC7170921.

In vivo protocol:

1: Li L, Pan Z, Ning D, Fu Y. Rosmanol and Carnosol Synergistically Alleviate Rheumatoid Arthritis through Inhibiting TLR4/NF-κB/MAPK Pathway. Molecules. 2021 Dec 23;27(1):78. doi: 10.3390/molecules27010078. PMID: 35011304; PMCID: PMC8746366. 2: Lu S, Li Y, Shen Q, Zhang W, Gu X, Ma M, Li Y, Zhang L, Liu X, Zhang X. Carnosol and its analogues attenuate muscle atrophy and fat lipolysis induced by cancer cachexia. J Cachexia Sarcopenia Muscle. 2021 Jun;12(3):779-795. doi: 10.1002/jcsm.12710. Epub 2021 May 5. PMID: 33951335; PMCID: PMC8200431. 3: O'Neill EJ, Hartogh DJD, Azizi K, Tsiani E. Anticancer Properties of Carnosol: A Summary of in Vitro and In Vivo Evidence. Antioxidants (Basel). 2020 Oct 8;9(10):961. doi: 10.3390/antiox9100961. PMID: 33049974; PMCID: PMC7600884. 4: Chun KS, Kundu J, Chae IG, Kundu JK. Carnosol: a phenolic diterpene with cancer chemopreventive potential. J Cancer Prev. 2014 Jun;19(2):103-10. doi: 10.15430/JCP.2014.19.2.103. PMID: 25337578; PMCID: PMC4204164. 5: Samarghandian S, Azimi-Nezhad M, Farkhondeh T. Anti-Carcinogenic Effects of Carnosol-An Updated Review. Curr Drug Discov Technol. 2018;15(1):32-40. doi: 10.2174/1570163814666170413121732. PMID: 28412913. 6: Yang L, Sui Y, Zhong L, Ma T, Ma Z, Liu X. Carnosol inhibits the growth and biofilm of Candida albicans. J Mycol Med. 2022 May;32(2):101234. doi: 10.1016/j.mycmed.2021.101234. Epub 2021 Dec 11. PMID: 34929524. 7: Johnson JJ. Carnosol: a promising anti-cancer and anti-inflammatory agent. Cancer Lett. 2011 Jun 1;305(1):1-7. doi: 10.1016/j.canlet.2011.02.005. Epub 2011 Mar 5. PMID: 21382660; PMCID: PMC3070765. 8: Alsamri H, Hasasna HE, Baby B, Alneyadi A, Dhaheri YA, Ayoub MA, Eid AH, Vijayan R, Iratni R. Carnosol Is a Novel Inhibitor of p300 Acetyltransferase in Breast Cancer. Front Oncol. 2021 May 13;11:664403. doi: 10.3389/fonc.2021.664403. PMID: 34055630; PMCID: PMC8155611. 9: Xiao WC, Zhou G, Wan L, Tu J, Yu YJ, She ZG, Xu CL, Wang L. Carnosol inhibits cerebral ischemia-reperfusion injury by promoting AMPK activation. Brain Res Bull. 2023 Apr;195:37-46. doi: 10.1016/j.brainresbull.2023.02.003. Epub 2023 Feb 10. PMID: 36775042. 10: Kashyap D, Kumar G, Sharma A, Sak K, Tuli HS, Mukherjee TK. Mechanistic insight into carnosol-mediated pharmacological effects: Recent trends and advancements. Life Sci. 2017 Jan 15;169:27-36. doi: 10.1016/j.lfs.2016.11.013. Epub 2016 Nov 18. PMID: 27871947. 11: Li Q, Zhang X, Li S, Li W, Teng Y, Zhou Y, Xiong H. Carnosol alleviates sevoflurane-induced cognitive dysfunction by mediating NF-κB pathway in aged rats. Drug Dev Res. 2022 Sep;83(6):1342-1350. doi: 10.1002/ddr.21963. Epub 2022 Jul 4. PMID: 35781309. 12: Mohebati A, Guttenplan JB, Kochhar A, Zhao ZL, Kosinska W, Subbaramaiah K, Dannenberg AJ. Retraction: Carnosol, a Constituent of Zyflamend, Inhibits Aryl Hydrocarbon Receptor-Mediated Activation of CYP1A1 and CYP1B1 Transcription and Mutagenesis. Cancer Prev Res (Phila). 2022 Jun 2;15(6):412. doi: 10.1158/1940-6207.CAPR-22-0203. PMID: 35652229; PMCID: PMC9272761. 13: Yan Y, Liu Y, Yang Y, Ding Y, Sun X. Carnosol suppresses microglia cell inflammation and apoptosis through PI3K/AKT/mTOR signaling pathway. Immunopharmacol Immunotoxicol. 2022 Oct;44(5):656-662. doi: 10.1080/08923973.2022.2074448. Epub 2022 Jun 6. PMID: 35521965. 14: D'Agata V, D'Amico AG, Maugeri G, Bucolo C, Rossi S, Giunta S. Carnosol attenuates high glucose damage in human retinal endothelial cells through regulation of ERK/Nrf2/HO-1 pathway. J Asian Nat Prod Res. 2023 Jul- Aug;25(8):783-795. doi: 10.1080/10286020.2022.2137022. Epub 2022 Oct 27. PMID: 36300534. 15: Lee JE, Im DS. Suppressive Effect of Carnosol on Ovalbumin-Induced Allergic Asthma. Biomol Ther (Seoul). 2021 Jan 1;29(1):58-63. doi: 10.4062/biomolther.2020.050. PMID: 32632049; PMCID: PMC7771837. 16: de Oliveira MR. The Dietary Components Carnosic Acid and Carnosol as Neuroprotective Agents: a Mechanistic View. Mol Neurobiol. 2016 Nov;53(9):6155-6168. doi: 10.1007/s12035-015-9519-1. Epub 2015 Nov 9. PMID: 26553346. 17: Avila-Carrasco L, Majano P, Sánchez-Toméro JA, Selgas R, López-Cabrera M, Aguilera A, González Mateo G. Natural Plants Compounds as Modulators of Epithelial-to-Mesenchymal Transition. Front Pharmacol. 2019 Jul 30;10:715. doi: 10.3389/fphar.2019.00715. PMID: 31417401; PMCID: PMC6682706. 18: Lo YC, Lin YC, Huang YF, Hsieh CP, Wu CC, Chang IL, Chen CL, Cheng CH, Chen HY. Carnosol-Induced ROS Inhibits Cell Viability of Human Osteosarcoma by Apoptosis and Autophagy. Am J Chin Med. 2017;45(8):1761-1772. doi: 10.1142/S0192415X17500951. Epub 2017 Nov 9. PMID: 29121803. 19: Alsamri H, Alneyadi A, Muhammad K, Ayoub MA, Eid A, Iratni R. Carnosol Induces p38-Mediated ER Stress Response and Autophagy in Human Breast Cancer Cells. Front Oncol. 2022 May 31;12:911615. doi: 10.3389/fonc.2022.911615. PMID: 35712465; PMCID: PMC9194514. 20: Li Y, Lin S, Liu P, Huang J, Qiu J, Wen Z, Yuan J, Qiu H, Liu Y, Liu Q, Zhou T, Luo P, Guo H, Ma Y, Guo D, Mo G, Tang Y, Xu L, Liang D, Xu J, Ding Y, Zhang S. Carnosol suppresses RANKL-induced osteoclastogenesis and attenuates titanium particles-induced osteolysis. J Cell Physiol. 2021 Mar;236(3):1950-1966. doi: 10.1002/jcp.29978. Epub 2020 Jul 28. PMID: 32722851.