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

MedKoo CAT#: 412376

CAS#: 5957-80-2

Description: 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

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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 Quantity
5.0mg USD 477.0 2 Weeks
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Synonym: Carnosol; CCRIS7122; CCRIS-7122; CCRIS 7122; HSDB7680; HSDB-7680; HSDB 7680

IUPAC/Chemical Name: 2H-9,4a-(Epoxymethano)phenanthren-12-one, 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-, (4aR-(4aalpha,9alpha,10abeta))-

InChi Key: XUSYGBPHQBWGAD-CKNLXJGOSA-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+/m1/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

Product Data:

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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 66.0 199.74

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.

Recalculate based on batch purity %
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
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. 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.

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1: 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.

2: Zheng Y, Zhang Y, Zheng Y, Zhang N. Carnosol protects against renal ischemia- reperfusion injury in rats. Exp Anim. 2018 Nov 1;67(4):545-553. doi: 10.1538/expanim.18-0067. Epub 2018 Jul 31. PMID: 30068825; PMCID: PMC6219873.

3: Lin C, Zhang X, Su Z, Xiao J, Lv M, Cao Y, Chen Y. Carnosol Improved Lifespan and Healthspan by Promoting Antioxidant Capacity in Caenorhabditis elegans. Oxid Med Cell Longev. 2019 Jun 24;2019:5958043. doi: 10.1155/2019/5958043. PMID: 31341531; PMCID: PMC6612998.

4: Yeo IJ, Park JH, Jang JS, Lee DY, Park JE, Choi YE, Joo JH, Song JK, Jeon HO, Hong JT. Inhibitory effect of Carnosol on UVB-induced inflammation via inhibition of STAT3. Arch Pharm Res. 2019 Mar;42(3):274-283. doi: 10.1007/s12272-018-1088-1. Epub 2018 Nov 15. PMID: 30430364; PMCID: PMC6426997.

5: 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.

6: Alsamri H, El Hasasna H, Al Dhaheri Y, Eid AH, Attoub S, Iratni R. Carnosol, a Natural Polyphenol, Inhibits Migration, Metastasis, and Tumor Growth of Breast Cancer via a ROS-Dependent Proteasome Degradation of STAT3. Front Oncol. 2019 Aug 8;9:743. doi: 10.3389/fonc.2019.00743. PMID: 31456939; PMCID: PMC6698796.

7: Li X, Zhao L, Han JJ, Zhang F, Liu S, Zhu L, Wang ZZ, Zhang GX, Zhang Y. Carnosol Modulates Th17 Cell Differentiation and Microglial Switch in Experimental Autoimmune Encephalomyelitis. Front Immunol. 2018 Aug 13;9:1807. doi: 10.3389/fimmu.2018.01807. PMID: 30150982; PMCID: PMC6100297.

8: 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.

9: Vlavcheski F, Baron D, Vlachogiannis IA, MacPherson REK, Tsiani E. Carnosol Increases Skeletal Muscle Cell Glucose Uptake via AMPK-Dependent GLUT4 Glucose Transporter Translocation. Int J Mol Sci. 2018 Apr 29;19(5):1321. doi: 10.3390/ijms19051321. PMID: 29710819; PMCID: PMC5983837.

10: Yan M, Vemu B, Veenstra J, Petiwala SM, Johnson JJ. Carnosol, a dietary diterpene from rosemary (Rosmarinus officinalis) activates Nrf2 leading to sestrin 2 induction in colon cells. Integr Mol Med. 2018 Aug;5(4):10.15761/IMM.1000335. doi: 10.15761/IMM.1000335. Epub 2018 Aug 15. PMID: 30972223; PMCID: PMC6453141.