Astaxanthin | CAS#472-61-7 | keto-carotenoid

MedKoo Cat#: 600113 | Name: Astaxanthin

Description:

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

Astaxanthin is a keto-carotenoid. Astaxanthin, unlike several carotenes and one other known carotenoid, is not converted to vitamin A (retinol) in the human body. Like other carotenoids, astaxanthin has self-limited absorption orally and such low toxicity by mouth that no toxic syndrome is known. It is an antioxidant with a slightly lower antioxidant activity in some model systems than other carotenoids. However, in living organisms the free-radical terminating effectiveness of each carotenoid is heavily modified by its lipid solubility, and thus varies with the type of system being protected. While astaxanthin is a natural dietary component, it can also be used as a food supplement. The supplement is intended for human, animal, and aquaculture consumption. The commercial production of astaxanthin comes from both natural and synthetic sources.

Chemical Structure

Astaxanthin

CAS#472-61-7

Theoretical Analysis

MedKoo Cat#: 600113

Name: Astaxanthin

CAS#: 472-61-7

Chemical Formula: C40H52O4

Exact Mass: 596.3866

Molecular Weight: 596.84

Elemental Analysis: C, 80.50; H, 8.78; O, 10.72

Price and Availability

Size	Price	Availability
50mg	USD 150.00	Ready to ship
100mg	USD 250.00	Ready to ship
200mg	USD 450.00	Ready to ship
500mg	USD 750.00	Ready to ship
1g	USD 1,250.00	2 Weeks
2g	USD 2,050.00	2 Weeks
5g	USD 3,650.00	2 Weeks

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Related CAS #

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Synonym

Astaxanthin.

IUPAC/Chemical Name

(6S)-6-Hydroxy-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexenyl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethyl-1-cyclohex-2-enone

InChi Key

MQZIGYBFDRPAKN-UWFIBFSHSA-N

InChi Code

InChI=1S/C40H52O4/c1-27(17-13-19-29(3)21-23-33-31(5)37(43)35(41)25-39(33,7)8)15-11-12-16-28(2)18-14-20-30(4)22-24-34-32(6)38(44)36(42)26-40(34,9)10/h11-24,35-36,41-42H,25-26H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,27-15+,28-16+,29-19+,30-20+/t35-,36-/m0/s1

SMILES Code

O=C1C(C)=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C([C@@H](O)CC2(C)C)=O)C(C)(C)C[C@@H]1O

Appearance

Red to purple 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#B7B12C06

QC Data

View QC data: current batch, Lot#B7B12C06

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Astaxanthin is a modulator of PPARγ and a potent antioxidant with antiproliferative, neuroprotective and anti-inflammatory activity.

In vitro activity:

In this study, the blastocyst yield, and diameter and total cell number per blastocyst were improved when the oocytes were treated with Ax (astaxanthin) during aging in vitro, suggesting that Ax could enhance the capacity of embryos to develop to the blastocyst stage and the embryo quality. The maternal gene in oocytes is required for preimplantation embryo development. Differences in maternal gene expression lead to the lower developmental potential of aged oocytes. For instance, ZAR1 plays essential role in transition from oocyte to embryo, and its expression in this study was found to be reduced in aged oocytes. Furthermore, Ax treatment was helpful to maintain the maternal gene expression for C-MOS, CCNB1, BMP15, CDX2 and POU5F1 in aged oocytes. The results also showed that the mRNA levels of CDX2 and POU5F1 genes were also increased in resultant blastocysts from Ax-treated aged oocytes. These two genes are required for differentiation of trophectoderm during early embryo development. Therefore, the above findings provided the most direct proof of the beneficial effects of Ax for aged oocytes. Reference: Sci Rep. 2020; 10: 20217. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7677382

In vivo activity:

The severe ER stress observed in response to ethanol was notably inhibited in the presence of AST (astaxanthin), demonstrating the anti-ER stress function of AST. ER stress can be activated by three UPR pathways, PERK-eIF2α-ATF4, ATF6 and IRE1-XBP1, which were also examined in this study. Vardiac levels of p-PERK, p-eif2α, ATF4, ATF-6, p-IRE1, and XBP-1 were all significantly increased in ethanol-treated mice (Fig. 3E–H), indicating that the three UPR pathways were all involved in ethanol-induced cardiac ER stress. However, activation of the three UPR pathways induced by ethanol was significantly inhibited by AST treatment (Fig. 3E– H), suggesting that AST may affect the same upstream regulatory factors of the three pathways. Based on these results, expression of cardiac GRP78 was assessed. Results showed that ethanol induced, while AST reversed, cardiac GRP78 expression (Fig. 3E&I), indicating that cardiac GRP78 is the target by which AST inhibited all UPR pathways induced by ethanol. Reference: Toxicol Appl Pharmacol. 2021 Feb 1; 412: 115378. https://www.sciencedirect.com/science/article/pii/S0041008X20305007?via%3Dihub

	Solvent	mg/mL	mM
Solubility
	DMSO	51.0	85.45

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 596.84 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. Jia BY, Xiang DC, Shao QY, Zhang B, Liu SN, Hong QH, Quan GB, Wu GQ. Inhibitory effects of astaxanthin on postovulatory porcine oocyte aging in vitro. Sci Rep. 2020 Nov 19;10(1):20217. doi: 10.1038/s41598-020-77359-6. PMID: 33214659; PMCID: PMC7677382. 2. Chao CT, Yeh HY, Tsai YT, Yuan TH, Liao MT, Huang JW, Chen HW. Astaxanthin Counteracts Vascular Calcification In Vitro Through an Early Up-Regulation of SOD2 Based on a Transcriptomic Approach. Int J Mol Sci. 2020 Nov 12;21(22):8530. doi: 10.3390/ijms21228530. PMID: 33198315; PMCID: PMC7698184. 3. Wang W, Liu T, Liu Y, Yu L, Yan X, Weng W, Lu X, Zhang C. Astaxanthin attenuates alcoholic cardiomyopathy via inhibition of endoplasmic reticulum stress-mediated cardiac apoptosis. Toxicol Appl Pharmacol. 2021 Feb 1;412:115378. doi: 10.1016/j.taap.2020.115378. Epub 2021 Jan 2. PMID: 33352188. 4. Zhuge F, Ni Y, Wan C, Liu F, Fu Z. Anti-diabetic effects of astaxanthin on an STZ-induced diabetic model in rats. Endocr J. 2021 Apr 28;68(4):451-459. doi: 10.1507/endocrj.EJ20-0699. Epub 2020 Dec 2. PMID: 33268598

In vitro protocol:

In vivo protocol:

1. Wang W, Liu T, Liu Y, Yu L, Yan X, Weng W, Lu X, Zhang C. Astaxanthin attenuates alcoholic cardiomyopathy via inhibition of endoplasmic reticulum stress-mediated cardiac apoptosis. Toxicol Appl Pharmacol. 2021 Feb 1;412:115378. doi: 10.1016/j.taap.2020.115378. Epub 2021 Jan 2. PMID: 33352188. 2. Zhuge F, Ni Y, Wan C, Liu F, Fu Z. Anti-diabetic effects of astaxanthin on an STZ-induced diabetic model in rats. Endocr J. 2021 Apr 28;68(4):451-459. doi: 10.1507/endocrj.EJ20-0699. Epub 2020 Dec 2. PMID: 33268598

1: Higuera-Ciapara I, Félix-Valenzuela L, Goycoolea FM. Astaxanthin: a review of its chemistry and applications. Crit Rev Food Sci Nutr. 2006;46(2):185-96. doi: 10.1080/10408690590957188. PMID: 16431409. 2: Davinelli S, Nielsen ME, Scapagnini G. Astaxanthin in Skin Health, Repair, and Disease: A Comprehensive Review. Nutrients. 2018 Apr 22;10(4):522. doi: 10.3390/nu10040522. PMID: 29690549; PMCID: PMC5946307. 3: Kishimoto Y, Yoshida H, Kondo K. Potential Anti-Atherosclerotic Properties of Astaxanthin. Mar Drugs. 2016 Feb 5;14(2):35. doi: 10.3390/md14020035. PMID: 26861359; PMCID: PMC4771988. 4: Chang MX, Xiong F. Astaxanthin and its Effects in Inflammatory Responses and Inflammation-Associated Diseases: Recent Advances and Future Directions. Molecules. 2020 Nov 16;25(22):5342. doi: 10.3390/molecules25225342. PMID: 33207669; PMCID: PMC7696511. 5: Stachowiak B, Szulc P. Astaxanthin for the Food Industry. Molecules. 2021 May 2;26(9):2666. doi: 10.3390/molecules26092666. PMID: 34063189; PMCID: PMC8125449. 6: Kumar S, Kumar R; Diksha; Kumari A, Panwar A. Astaxanthin: A super antioxidant from microalgae and its therapeutic potential. J Basic Microbiol. 2022 Sep;62(9):1064-1082. doi: 10.1002/jobm.202100391. Epub 2021 Nov 24. PMID: 34817092. 7: Li J, Guo C, Wu J. Astaxanthin in Liver Health and Disease: A Potential Therapeutic Agent. Drug Des Devel Ther. 2020 Jun 9;14:2275-2285. doi: 10.2147/DDDT.S230749. PMID: 32606597; PMCID: PMC7293384. 8: Nishida Y, Nawaz A, Hecht K, Tobe K. Astaxanthin as a Novel Mitochondrial Regulator: A New Aspect of Carotenoids, beyond Antioxidants. Nutrients. 2021 Dec 27;14(1):107. doi: 10.3390/nu14010107. PMID: 35010981; PMCID: PMC8746862. 9: Si P, Zhu C. Biological and neurological activities of astaxanthin (Review). Mol Med Rep. 2022 Oct;26(4):300. doi: 10.3892/mmr.2022.12816. Epub 2022 Aug 10. PMID: 35946443; PMCID: PMC9435021. 10: Brendler T, Williamson EM. Astaxanthin: How much is too much? A safety review. Phytother Res. 2019 Dec;33(12):3090-3111. doi: 10.1002/ptr.6514. Epub 2019 Dec 1. PMID: 31788888. 11: Kohandel Z, Farkhondeh T, Aschner M, Pourbagher-Shahri AM, Samarghandian S. Anti-inflammatory action of astaxanthin and its use in the treatment of various diseases. Biomed Pharmacother. 2022 Jan;145:112179. doi: 10.1016/j.biopha.2021.112179. Epub 2021 Nov 1. PMID: 34736076. 12: Giannaccare G, Pellegrini M, Senni C, Bernabei F, Scorcia V, Cicero AFG. Clinical Applications of Astaxanthin in the Treatment of Ocular Diseases: Emerging Insights. Mar Drugs. 2020 May 1;18(5):239. doi: 10.3390/md18050239. PMID: 32370045; PMCID: PMC7281326. 13: Kim SH, Kim H. Inhibitory Effect of Astaxanthin on Oxidative Stress-Induced Mitochondrial Dysfunction-A Mini-Review. Nutrients. 2018 Aug 21;10(9):1137. doi: 10.3390/nu10091137. PMID: 30134611; PMCID: PMC6165470. 14: Tominaga K, Hongo N, Karato M, Yamashita E. Cosmetic benefits of astaxanthin on humans subjects. Acta Biochim Pol. 2012;59(1):43-7. Epub 2012 Mar 17. PMID: 22428137. 15: Mota GCP, Moraes LBS, Oliveira CYB, Oliveira DWS, Abreu JL, Dantas DMM, Gálvez AO. Astaxanthin from Haematococcus pluvialis: processes, applications, and market. Prep Biochem Biotechnol. 2022;52(5):598-609. doi: 10.1080/10826068.2021.1966802. Epub 2021 Aug 23. PMID: 34424829. 16: Kidd P. Astaxanthin, cell membrane nutrient with diverse clinical benefits and anti-aging potential. Altern Med Rev. 2011 Dec;16(4):355-64. PMID: 22214255. 17: Kohandel Z, Farkhondeh T, Aschner M, Samarghandian S. Nrf2 a molecular therapeutic target for Astaxanthin. Biomed Pharmacother. 2021 May;137:111374. doi: 10.1016/j.biopha.2021.111374. Epub 2021 Feb 18. PMID: 33761600. 18: Ota T. Prevention of NAFLD/NASH by Astaxanthin and β-Cryptoxanthin. Adv Exp Med Biol. 2021;1261:231-238. doi: 10.1007/978-981-15-7360-6_21. PMID: 33783746. 19: Singh KN, Patil S, Barkate H. Protective effects of astaxanthin on skin: Recent scientific evidence, possible mechanisms, and potential indications. J Cosmet Dermatol. 2020 Jan;19(1):22-27. doi: 10.1111/jocd.13019. Epub 2019 May 29. PMID: 31141292. 20: Zhang C, Chen X, Too HP. Microbial astaxanthin biosynthesis: recent achievements, challenges, and commercialization outlook. Appl Microbiol Biotechnol. 2020 Jul;104(13):5725-5737. doi: 10.1007/s00253-020-10648-2. Epub 2020 May 13. PMID: 32399589.