Showing Compound (3S,3'S)-Astaxanthin (FDB018640)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:50 UTC

Update date

2018-05-29 01:37:57 UTC

Primary ID

FDB018640

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(3S,3'S)-Astaxanthin

Description

Astaxanthin (pronounced as-tuh-zan'-thin) is a carotenoid. It belongs to a larger class of phytochemicals known as terpenes. It is classified as a xanthophyll, which means "yellow leaves". Like many carotenoids, it is a colorful, lipid-soluble pigment. Astaxanthin is produced by microalgae, yeast, salmon, trout, krill, shrimp, crayfish, crustaceans, and the feathers of some birds. Professor Basil Weedon was the first to map the structure of astaxanthin.; Astaxanthin is the main carotenoid pigment found in aquatic animals. It is also found in some birds, such as flamingoes, quails, and other species. This carotenoid is included in many well-known seafoods such as salmon, trout, red seabream, shrimp, lobster, and fish eggs. Astaxanthin, similar to other carotenoids, cannot be synthesized by animals and must be provided in the diet. Mammals, including humans, lack the ability to synthesize astaxanthin or to convert dietary astaxanthin into vitamin A. Astaxanthin belongs to the xanthophyll class of carotenoids. It is closely related to beta-carotene, lutein, and zeaxanthin, sharing with them many of the general metabolic and physiological functions attributed to carotenoids. In addition, astaxanthin has unique chemical properties based on its molecular structure. The presence of the hydroxyl (OH) and keto (CdO) moieties on each ionone ring explains some of its unique features, namely, the ability to be esterified and a higher antioxidant activity and a more polar nature than other carotenoids. In its free form, astaxanthin is considerably unstable and particularly susceptible to oxidation. Hence it is found in nature either conjugated with proteins (e.g., salmon muscle or lobster exoskeleton) or esterified with one or two fatty acids (monoester and diester forms), which stabilize the molecule. Various astaxanthin isomers have been characterized on the basis of the configuration of the two hydroxyl groups on the molecule. the geometrical and optical isomers of astaxanthin are distributed selectively in different tissues and that levels of free astaxanthin in the liver are greater than the corresponding concentration in the plasma, suggesting concentrative uptake by the liver. Astaxanthin, similar to other carotenoids, is a very lipophilic compound and has a low oral bioavailability. This criterion has limited the ability to test this compound in well-defined rodent models of human disease. (PMID: 16562856); Astaxanthin is a carotenoid widely used in salmonid and crustacean aquaculture to provide the pink color characteristic of that species. This application has been well documented for over two decades and is currently the major market driver for the pigment. Additionally, astaxanthin also plays a key role as an intermediary in reproductive processes. Synthetic astaxanthin dominates the world market but recent interest in natural sources of the pigment has increased substantially. Common sources of natural astaxanthin are the green algae Haematococcus pluvialis, the red yeast, Phaffia rhodozyma, as well as crustacean byproducts. Astaxanthin possesses an unusual antioxidant activity which has caused a surge in the nutraceutical market for the encapsulated productand is) also, health benefits such as cardiovascular disease prevention, immune system boosting, bioactivity against Helycobacter pylori, and cataract prevention, have been associated with astaxanthin consumption. Research on the health benefits of astaxanthin is very recent and has mostly been performed in vitro or at the pre-clinical level with humans. (PMID: 16431409); Astaxanthin, unlike some carotenoids, does not convert to Vitamin A (retinol) in the human body. Too much Vitamin A is toxic for a human, but astaxanthin is not. However, it is a powerful antioxidant; it is claimed to be 10 times more capable than other carotenoids. However, other sources suggest astaxanthin has slightly lower antioxidant activity than other carotenoids.; While astaxanthin is a natural nutritional component, it can be found 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.

CAS Number

472-61-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Show entries

Search:

Synonym	Source
(3R,3's)-3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione	HMDB
(3R,3's)-Astaxanthin	HMDB
(3S,3'S)-3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione	biospider
(3S,3'S)-all-trans-Astaxanthin	biospider
(3S,3'S)-Astaxanthin	biospider
3,3'-Dihydroxy-,-carotene-4,4'-dione	biospider
3,3'-dihydroxy-4,4'-diketo-beta,beta-carotene	biospider
3,3'-Dihydroxy-b,b-carotene-4,4'-dione	Generator
3,3'-Dihydroxy-b-carotene-4,4'-dione	Generator
3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione	biospider

Showing 1 to 10 of 35 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.00067 g/L	ALOGPS
logP	7.4	ALOGPS
logP	8.05	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	13.07	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	195.98 m³·mol⁻¹	ChemAxon
Polarizability	72.68 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C40H52O4

IUPAC name

6-hydroxy-3-[(1E,3E,5E,7E,9E,11Z,13E,15E,17E)-18-(4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

InChI Identifier

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+

InChI Key

MQZIGYBFDRPAKN-HDQLMXHPSA-N

Isomeric SMILES

C\C(\C=C\C=C(/C)\C=C\C1=C(C)C(=O)C(O)CC1(C)C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)C(O)CC1(C)C

Average Molecular Weight

596.8385

Monoisotopic Molecular Weight

596.386560152

Classification

Description

Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Xanthophylls

Alternative Parents

Substituents

Xanthophyll
Cyclohexenone
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Subcellular:

Source:

Biological:

Animal

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 80.50%; H 8.78%; O 10.72%	DFC
Melting Point	Mp 223-225°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(3S,3'S)-Astaxanthin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-2000090000-c6336112eb898c2f0a48	Spectrum
Predicted GC-MS	(3S,3'S)-Astaxanthin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0udi-3000019000-6b5720849187b199d6bf	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0232390000-f37e3530214c99f63306	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-1296830000-ac8ea41a53a053acb7c8	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03fr-0185910000-7af6a00762ad7e8ee75d	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000090000-248171e80348a7e1d17e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0000090000-b9759de23c7494bb7b2d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0333390000-074ea5de5d017bafdb5e	2016-08-03	View Spectrum