Transcrocetin | Crocetin | Trans-crocetin | CAS#591230-99-8 | 27876-94-4 | 64603-92-5 | anticarcinogenic agent

MedKoo Cat#: 329599 | Name: Transcrocetin

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Description:

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

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.

Chemical Structure

Transcrocetin

CAS#27876-94-4 (free acid)

Theoretical Analysis

MedKoo Cat#: 329599

Name: Transcrocetin

CAS#: 27876-94-4 (free acid)

Chemical Formula: C20H24O4

Exact Mass: 328.1675

Molecular Weight: 328.41

Elemental Analysis: C, 73.15; H, 7.37; O, 19.49

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,250.00	Ready to ship
500mg	USD 2,850.00	Ready to ship

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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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#B7P05F12

QC Data

View QC data: current batch, Lot#B7P05F12

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

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	mg/mL	mM
Solubility
	DMSO	1.0	3.05

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 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:

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: Abdian S, Fakhri S, Moradi SZ, Khirehgesh MR, Echeverría J. Saffron and its major constituents against neurodegenerative diseases: A mechanistic review. Phytomedicine. 2024 Dec;135:156097. doi: 10.1016/j.phymed.2024.156097. Epub 2024 Sep 27. PMID: 39577115. 2: Xue C, Zhang J, Zhang C, Hu Z, Liu H, Mo L, Li M, Lou A, Shen Q, Luo J, Wang S, Quan W. Augmenting antioxidative capacity of myosin and cytoprotective potential of myosin digestion products through the integration of crocin and crocetin: A comprehensive analysis via quantum chemical computing and molecular dynamics. Food Chem. 2025 Feb 15;465(Pt 2):142053. doi: 10.1016/j.foodchem.2024.142053. Epub 2024 Nov 14. PMID: 39561599. 3: Rajabian F, Razavi BM, Mehri S, Amouian S, Ghasemzadeh Rahbardar M, Khajavi Rad A, Hosseinzadeh H. Evaluation of pathways involved in the protective effect of trans sodium crocetinate against contrast-induced nephropathy in rats. Naunyn Schmiedebergs Arch Pharmacol. 2024 Nov 16. doi: 10.1007/s00210-024-03600-y. Epub ahead of print. PMID: 39549062. 4: Wang X, Zhuhuang C, He Y, Zhang X, Wang Y, Ni Q, Zhang Y, Xu G. Selective transformation of crocin-1 to crocetin-glucosyl esters by β-glucosidase (Lf18920) from Leifsonia sp. ZF2019: Insights from molecular docking and point mutations. Enzyme Microb Technol. 2024 Dec;181:110522. doi: 10.1016/j.enzmictec.2024.110522. Epub 2024 Oct 4. PMID: 39378560. 5: Moradzadeh M, Kargar M, Erfanian S, Haghshenas MR, Hojjat-Farsangi M, Rahmanian K, Sotoodeh Jahromi A. Effect of Crocin and Crocetin Compared to Cyclophosphamide on the Expression Level of miRNA-16-1 in a B Cell Transformed with EBV Virus Cell Line. Asian Pac J Cancer Prev. 2024 Sep 1;25(9):3179-3185. doi: 10.31557/APJCP.2024.25.9.3179. PMID: 39342597; PMCID: PMC11700333. 6: García CJ, Beltrán D, Frutos-Lisón MD, García-Conesa MT, Tomás-Barberán FA, García-Villalba R. New findings in the metabolism of the saffron apocarotenoids, crocins and crocetin, by the human gut microbiota. Food Funct. 2024 Sep 16;15(18):9315-9329. doi: 10.1039/d4fo02233e. PMID: 39171480. 7: Tsai WE, Liu YT, Kuo FH, Cheng WY, Shen CC, Chiao MT, Huang YF, Liang YJ, Yang YC, Hsieh WY, Chen JP, Liu SY, Chiu CD. Crocetin Enhances Temozolomide Efficacy in Glioblastoma Therapy Through Multiple Pathway Suppression. Curr Neurovasc Res. 2024;21(3):320-336. doi: 10.2174/0115672026332275240731054001. PMID: 39092730. 8: Tong Z, Jie X, Chen Z, Deng M, Li X, Zhang Z, Pu F, Xie Z, Xu Z, Wang P. Borneol and lactoferrin dual-modified crocetin-loaded nanoliposomes enhance neuroprotection in HT22 cells and brain targeting in mice. Eur J Med Chem. 2024 Oct 5;276:116674. doi: 10.1016/j.ejmech.2024.116674. Epub 2024 Jul 14. PMID: 39004017. 9: Naraki K, Ghasemzadeh Rahbardar M, Razavi BM, Aminifar T, Khajavi Rad A, Amoueian S, Hosseinzadeh H. The power of trans-sodium crocetinate: exploring its renoprotective effects in a rat model of colistin-induced nephrotoxicity. Naunyn Schmiedebergs Arch Pharmacol. 2024 Dec;397(12):10155-10174. doi: 10.1007/s00210-024-03259-5. Epub 2024 Jul 12. PMID: 38995374. 10: Ajzashokouhi AH, Razavi BM, Sadeghian H, Hosseinzadeh H. In vivo and in vitro effects of crocetin and its amide derivative on acrylamide- induced neurotoxicity. Avicenna J Phytomed. 2024 Jan-Feb;14(1):78-89. doi: 10.22038/AJP.2023.22316. PMID: 38948176; PMCID: PMC11210700. 11: Zhu J, Jia W, Peng J. Dissecting the binding effect of Crocetin glucosyltransferase 2 in crocetin biotransformation in saffron (Crocus sativus L.) from different origins. Food Chem. 2024 Oct 15;455:139917. doi: 10.1016/j.foodchem.2024.139917. Epub 2024 May 31. PMID: 38838622. 12: Paramanya S, Lee JH, Lee J. Antibiofilm activity of carotenoid crocetin against Staphylococcal strains. Front Cell Infect Microbiol. 2024 May 13;14:1404960. doi: 10.3389/fcimb.2024.1404960. PMID: 38803574; PMCID: PMC11128560. 13: Hui B, Zhang X, Wang S, Shu Y, Li R, Yang Z. Crocetin preconditioning attenuates ischemia reperfusion-induced hepatic injury by disrupting Keap1/Nrf2 interaction and activating Nrf2/HO-1 pathway. Tissue Cell. 2024 Jun;88:102411. doi: 10.1016/j.tice.2024.102411. Epub 2024 May 21. PMID: 38781791. 14: Banaeeyeh S, Afkhami-Goli A, Moosavi Z, Razavi BM, Hosseinzadeh H. Anti- inflammatory, antioxidant and anti-mitophagy effects of trans sodium crocetinate on experimental autoimmune encephalomyelitis in BALB/C57 mice. Metab Brain Dis. 2024 Jun;39(5):783-801. doi: 10.1007/s11011-024-01349-0. Epub 2024 May 13. PMID: 38739183. 15: Li B, Zhang Y, Yang Z, Li X, Yang J, Luo K, Wang R, Xiao C, Li M, Gao Y. Iodine-induced synthetic method and pharmacokinetic study of cis- and trans- crocetin. Front Pharmacol. 2024 Apr 9;15:1364286. doi: 10.3389/fphar.2024.1364286. PMID: 38655182; PMCID: PMC11035770. 16: Aminifard T, Mehri S, Ghasemzadeh Rahbardar M, Rajabian F, Khajavi Rad A, Hosseinzadeh H. Trans-sodium crocetinate suppresses apoptotic and oxidative response following myoglobin-induced cytotoxicity in HEK-293 cells. Iran J Basic Med Sci. 2024;27(6):768-774. doi: 10.22038/IJBMS.2024.75306.16322. PMID: 38645503; PMCID: PMC11024408. 17: Hasheminasab FS, Azimi M, Raeiszadeh M. Therapeutic effects of saffron (Crocus sativus L) on female reproductive system disorders: A systematic review. Phytother Res. 2024 Jun;38(6):2832-2846. doi: 10.1002/ptr.8186. Epub 2024 Apr 1. PMID: 38558480. 18: Wang L, Ma X, Pan Y, Ye H, Liu Z, Kuang Z, Zhao Z, Liu A, Ji Y. pH- Responsive Calcium Ions and Crocetin Releasing Hydrogel for Accelerating Skin Wound Healing. Chem Asian J. 2024 May 17;19(10):e202400198. doi: 10.1002/asia.202400198. Epub 2024 Apr 18. PMID: 38558255. 19: Leppert MH, Poisson SN, Scarbro S, Suresh K, Lisabeth LD, Putaala J, Schwamm LH, Daugherty SL, Bradley CJ, Burke JF, Ho PM. Association of Traditional and Nontraditional Risk Factors in the Development of Strokes Among Young Adults by Sex and Age Group: A Retrospective Case-Control Study. Circ Cardiovasc Qual Outcomes. 2024 Apr;17(4):e010307. doi: 10.1161/CIRCOUTCOMES.123.010307. Epub 2024 Mar 26. PMID: 38529631; PMCID: PMC11021148. 20: Liu C, Wang L, Zhou Y, Xia W, Wang Z, Kuang L, Hua D. Biogenic crocetin- crosslinked chitosan nanoparticles with high stability and drug loading for efficient radioprotection. Int J Biol Macromol. 2024 Apr;265(Pt 1):130756. doi: 10.1016/j.ijbiomac.2024.130756. Epub 2024 Mar 10. PMID: 38462118.