WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H329599
CAS#: 27876-94-4 (free acid)
Description: Crocetin, also known as Transcrocetin, is a natural apocarotenoid dicarboxylic acid that is found in the crocus flower and Gardenia jasminoides (fruits). Crocetin is also anticarcinogenic, antineoplastic, antioxidant and protective agent. It forms brick red crystals with a melting point of 285 °C. Crocetin protects ultraviolet A-induced oxidative stress and cell death in skin in vitro and in vivo. Crocetin protects against hypertension and cerebral thrombogenesis in stroke-prone spontaneously hypertensive rats. Crocin and crocetin may provide neuroprotection in rats by reducing the production of various neurotoxic molecules, based on an in-vitro cell study.
Hodoodo Cat#: H329599
Name: Transcrocetin
CAS#: 27876-94-4 (free acid)
Chemical Formula: C20H24O4
Exact Mass: 328.17
Molecular Weight: 328.408
Elemental Analysis: C, 73.15; H, 7.37; O, 19.49
Related CAS #: 591230-99-8 (sodium 1:2) 64603-92-5(sodium 1:x) 27876-94-4 (free acid) 189148-59-2 504-39-2 763872-89-5,
Synonym: Crotecin, Trans-crocetin; Transcrocetin; TSC; NSC 407300; Natural Yellow 6; 8,8'-Diapocarotenedioic acid. ,8'-Diapo-psi,psi-carotenedioic acid.
IUPAC/Chemical Name: (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioic acid
InChi Key: PANKHBYNKQNAHN-MQQNZMFNSA-N
InChi Code: InChI=1S/C20H24O4/c1-15(11-7-13-17(3)19(21)22)9-5-6-10-16(2)12-8-14-18(4)20(23)24/h5-14H,1-4H3,(H,21,22)(H,23,24)/b6-5+,11-7+,12-8+,15-9+,16-10+,17-13+,18-14+
SMILES Code: O=C(O)/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C(O)=O
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: >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:
| Biological target: | Transcrocetin (trans-Crocetin) acts as an NMDA receptor antagonist with high affinity. |
| In vitro activity: | The current study investigated the effects of crocetin on proliferation, migration, VEGF and MMP-9 expression, and signaling pathways in HCT-116 colorectal cancer cells. The initial data indicated that crocetin has a cytotoxic effect against HCT-116 cell line in in vitro model. Crocetin significantly down- regulated the expression of VEGF and MMP-9 mRNA levels in HCT-116 cells, suggesting a substantial anticancer capacity. An interesting finding of this study was significant and substantial down-regulation of both examined genes even at lower concentrations. The expression of p38 MAPK and FAK proteins, which are involved in cell proliferation, differentiation, migration, and metastasis, were assessed by western blot analyses. As shown in Fig. 4, crocetin induced the phosphorylation of p38 MAPK but not FAK compared to the non-treated control cells. The results showed that the phosphorylation levels of p-p38 MAPK molecules were significantly increased by crocetin at 400, 600, and 800 μM compared to the control group (P < 0.01), while crocetin had no evident effect on the expression of p-FAK. Reference: Res Pharm Sci. 2020 Dec; 15(6): 592–601. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8020854/ |
| In vivo activity: | A significant increase in ROS generation (red) was observed in the rat hearts from the ATO (arsenic trioxide) group in comparison with the Con group (Fig. 5). However, CRT (crocetin) preconditioning partially eliminated these changes (P<0.01), and ROS generation was markedly lower in the CRT-H group compared with the CRT-L group. Compared with the Con group, the ATO group had increased myocardial MDA (malondialdehyde) activity (P<0.01), but decreased SOD, GSH-Px and CAT activities (P<0.01) (Fig. 6A-D). Furthermore, CRT administration (20 and 40 mg/kg/day) led to a dose-dependent increase in SOD, GSH-Px and CAT activities (P<0.01 or P<0.05), along with a concomitant decrease in MDA content compared with the ATO group (P<0.01 or P<0.05). Therefore, CRT attenuated the oxidative stress associated with ATO-induced cardiotoxicity in a dose-dependent manner (P<0.01). Reference: Mol Med Rep. 2020 Dec; 22(6): 5271–5281. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7646993/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 1.0 | 3.05 |
The following data is based on the product molecular weight 328.41 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. Wen YL, Li Y, Zhu G, Zheng Z, Shi M, Qin S. Gene Expression Profiling and Biofunction Analysis of HepG2 Cells Targeted by Crocetin. Mediators Inflamm. 2021 Apr 1;2021:5512166. doi: 10.1155/2021/5512166. PMID: 33867857; PMCID: PMC8035019. 3. Khajeh E, Rasmi Y, Kheradmand F, Malekinejad H, Aramwit P, Saboory E, Daeihassani B, Nasirzadeh M. Crocetin suppresses the growth and migration in HCT-116 human colorectal cancer cells by activating the p-38 MAPK signaling pathway. Res Pharm Sci. 2020 Nov 27;15(6):592-601. doi: 10.4103/1735-5362.301344. PMID: 33828602; PMCID: PMC8020854.1. Zhao Z, Li J, Zheng B, Liang Y, Shi J, Zhang J, Han X, Chu L, Chu X, Gao Y. Ameliorative effects and mechanism of crocetin in arsenic trioxide‑induced cardiotoxicity in rats. Mol Med Rep. 2020 Dec;22(6):5271-5281. doi: 10.3892/mmr.2020.11587. Epub 2020 Oct 14. PMID: 33173984; PMCID: PMC7646993. 4. Dong N, Dong Z, Chen Y, Gu X. Crocetin Alleviates Inflammation in MPTP-Induced Parkinson's Disease Models through Improving Mitochondrial Functions. Parkinsons Dis. 2020 Oct 10;2020:9864370. doi: 10.1155/2020/9864370. PMID: 33101635; PMCID: PMC7569465. |
| In vitro protocol: | 1. Wen YL, Li Y, Zhu G, Zheng Z, Shi M, Qin S. Gene Expression Profiling and Biofunction Analysis of HepG2 Cells Targeted by Crocetin. Mediators Inflamm. 2021 Apr 1;2021:5512166. doi: 10.1155/2021/5512166. PMID: 33867857; PMCID: PMC8035019. 2. Khajeh E, Rasmi Y, Kheradmand F, Malekinejad H, Aramwit P, Saboory E, Daeihassani B, Nasirzadeh M. Crocetin suppresses the growth and migration in HCT-116 human colorectal cancer cells by activating the p-38 MAPK signaling pathway. Res Pharm Sci. 2020 Nov 27;15(6):592-601. doi: 10.4103/1735-5362.301344. PMID: 33828602; PMCID: PMC8020854. |
| In vivo protocol: | 1. Zhao Z, Li J, Zheng B, Liang Y, Shi J, Zhang J, Han X, Chu L, Chu X, Gao Y. Ameliorative effects and mechanism of crocetin in arsenic trioxide‑induced cardiotoxicity in rats. Mol Med Rep. 2020 Dec;22(6):5271-5281. doi: 10.3892/mmr.2020.11587. Epub 2020 Oct 14. PMID: 33173984; PMCID: PMC7646993. 2. Dong N, Dong Z, Chen Y, Gu X. Crocetin Alleviates Inflammation in MPTP-Induced Parkinson's Disease Models through Improving Mitochondrial Functions. Parkinsons Dis. 2020 Oct 10;2020:9864370. doi: 10.1155/2020/9864370. PMID: 33101635; PMCID: PMC7569465. |
1: Zhang Y, Fei F, Zhen L, Zhu X, Wang J, Li S, Geng J, Sun R, Yu X, Chen T, Feng S, Wang P, Yang N, Zhu Y, Huang J, Zhao Y, Aa J, Wang G. Sensitive analysis and simultaneous assessment of pharmacokinetic properties of crocin and crocetin after oral administration in rats. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Feb 15;1044-1045:1-7. doi: 10.1016/j.jchromb.2016.12.003. PubMed PMID: 28056427.
2: Karkoula E, Lemonakis N, Kokras N, Dalla C, Gikas E, Skaltsounis AL, Tsarbopoulos A. Development and validation of a UPLC method for quantifying trans-crocin 4 and crocetin from saffron in plasma: A pharmacokinetic study. Planta Med. 2016 Dec;81(S 01):S1-S381. PubMed PMID: 27976146.
3: Song L, Kang C, Sun Y, Huang W, Liu W, Qian Z. Crocetin Inhibits Lipopolysaccharide-Induced Inflammatory Response in Human Umbilical Vein Endothelial Cells. Cell Physiol Biochem. 2016;40(3-4):443-452. PubMed PMID: 27889767.
4: Tiribuzi R, Crispoltoni L, Chiurchiù V, Casella A, Montecchiani C, Del Pino AM, Maccarrone M, Palmerini CA, Caltagirone C, Kawarai T, Orlacchio A, Orlacchio A. Trans-crocetin improves amyloid-β degradation in monocytes from Alzheimer's Disease patients. J Neurol Sci. 2017 Jan 15;372:408-412. doi: 10.1016/j.jns.2016.11.004. PubMed PMID: 27865556.
5: Soltani F, Ramezani M, Amel Farzad S, Mokhtarzadeh A, Hashemi M. Comparison study of the effect of alkyl-modified and unmodified PAMAM and PPI dendrimers on solubility and antitumor activity of crocetin. Artif Cells Nanomed Biotechnol. 2016 Oct 31:1-7. [Epub ahead of print] PubMed PMID: 27797284.
6: Ray P, Guha D, Chakraborty J, Banerjee S, Adhikary A, Chakraborty S, Das T, Sa G. Crocetin exploits p53-induced death domain (PIDD) and FAS-associated death domain (FADD) proteins to induce apoptosis in colorectal cancer. Sci Rep. 2016 Sep 13;6:32979. doi: 10.1038/srep32979. PubMed PMID: 27622714; PubMed Central PMCID: PMC5020693.
7: Sapanidou V, Taitzoglou I, Tsakmakidis I, Kourtzelis I, Fletouris D, Theodoridis A, Lavrentiadou S, Tsantarliotou M. Protective effect of crocetin on bovine spermatozoa against oxidative stress during in vitro fertilization. Andrology. 2016 Nov;4(6):1138-1149. doi: 10.1111/andr.12248. PubMed PMID: 27575445.
8: Ohba T, Ishisaka M, Tsujii S, Tsuruma K, Shimazawa M, Kubo K, Umigai N, Iwawaki T, Hara H. Crocetin protects ultraviolet A-induced oxidative stress and cell death in skin in vitro and in vivo. Eur J Pharmacol. 2016 Oct 15;789:244-53. doi: 10.1016/j.ejphar.2016.07.036. PubMed PMID: 27452919.
9: Zullo G, De Canditiis C, Pero ME, Albero G, Salzano A, Neglia G, Campanile G, Gasparrini B. Crocetin improves the quality of in vitro-produced bovine embryos: Implications for blastocyst development, cryotolerance, and apoptosis. Theriogenology. 2016 Nov;86(8):1879-85. doi: 10.1016/j.theriogenology.2016.06.011. PubMed PMID: 27393222.
10: Hafezi Ghahestani Z, Alebooye Langroodi F, Mokhtarzadeh A, Ramezani M, Hashemi M. Evaluation of anti-cancer activity of PLGA nanoparticles containing crocetin. Artif Cells Nanomed Biotechnol. 2016 Jun 21:1-6. [Epub ahead of print] PubMed PMID: 27327450.
11: Huang Z, Nan C, Wang H, Su Q, Xue W, Chen Y, Shan X, Duan J, Chen G, Tao W. Crocetin ester improves myocardial ischemia via Rho/ROCK/NF-κB pathway. Int Immunopharmacol. 2016 Sep;38:186-93. doi: 10.1016/j.intimp.2016.05.025. PubMed PMID: 27285672.
12: Ahrazem O, Rubio-Moraga A, Argandoña-Picazo J, Castillo R, Gómez-Gómez L. Intron retention and rhythmic diel pattern regulation of carotenoid cleavage dioxygenase 2 during crocetin biosynthesis in saffron. Plant Mol Biol. 2016 Jun;91(3):355-74. doi: 10.1007/s11103-016-0473-8. PubMed PMID: 27071403; PubMed Central PMCID: PMC4884571.
13: Chen P, Chen Y, Wang Y, Cai S, Deng L, Liu J, Zhang H. Comparative Evaluation of Hepatoprotective Activities of Geniposide, Crocins and Crocetin by CCl4-Induced liver Injury in Mice. Biomol Ther (Seoul). 2016 Mar 1;24(2):156-62. doi: 10.4062/biomolther.2015.094. PubMed PMID: 26902084; PubMed Central PMCID: PMC4774496.
14: Ding J, Su J, Zhang L, Ma J. Crocetin Activates Foxp3 Through TIPE2 in Asthma-Associated Treg Cells. Cell Physiol Biochem. 2015;37(6):2425-33. doi: 10.1159/000438595. PubMed PMID: 26646898.
15: Bend JR, Xia XY, Chen D, Awaysheh A, Lo A, Rieder MJ, Rylett RJ. Attenuation of Oxidative Stress in HEK 293 Cells by the TCM Constituents Schisanhenol, Baicalein, Resveratrol or Crocetin and Two Defined Mixtures. J Pharm Pharm Sci. 2015;18(4):661-82. PubMed PMID: 26626254.
16: Amin B, Nakhsaz A, Hosseinzadeh H. Evaluation of the antidepressant-like effects of acute and sub-acute administration of crocin and crocetin in mice. Avicenna J Phytomed. 2015 Sep-Oct;5(5):458-68. PubMed PMID: 26468466; PubMed Central PMCID: PMC4599114.
17: Ordoudi SA, Kyriakoudi A, Tsimidou MZ. Enhanced Bioaccessibility of Crocetin Sugar Esters from Saffron in Infusions Rich in Natural Phenolic Antioxidants. Molecules. 2015 Sep 25;20(10):17760-74. doi: 10.3390/molecules201017760. PubMed PMID: 26404216.
18: Llorens S, Mancini A, Serrano-Díaz J, D'Alessandro AM, Nava E, Alonso GL, Carmona M. Effects of Crocetin Esters and Crocetin from Crocus sativus L. on Aortic Contractility in Rat Genetic Hypertension. Molecules. 2015 Sep 22;20(9):17570-84. doi: 10.3390/molecules200917570. PubMed PMID: 26402666.
19: Ahrazem O, Rubio-Moraga A, Berman J, Capell T, Christou P, Zhu C, Gómez-Gómez L. The carotenoid cleavage dioxygenase CCD2 catalysing the synthesis of crocetin in spring crocuses and saffron is a plastidial enzyme. New Phytol. 2016 Jan;209(2):650-63. doi: 10.1111/nph.13609. PubMed PMID: 26377696.
20: Tong Y, Yan Y, Zhu X, Liu R, Gong F, Zhang L, Wang P. Simultaneous quantification of crocetin esters and picrocrocin changes in Chinese saffron by high-performance liquid chromatography-diode array detector during 15 years of storage. Pharmacogn Mag. 2015 Jul-Sep;11(43):540-5. doi: 10.4103/0973-1296.160467. PubMed PMID: 26246729; PubMed Central PMCID: PMC4522840.
