Cryptoxanthin

Cryptoxanthin[1]
IUPAC name (R)-3,5,5-Trimethyl-4-[3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex- 1-enyl)-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-cyclohex-3-enol
Other names (3R)-β,β-Caroten-3-ol Cryptoxanthol Caricaxanthin (R)-all-trans-β-Caroten-3-ol Hydroxy-β-carotene
Identifiers
CAS number	472-70-8 Y
PubChem	5281235
ChemSpider	4444647 Y
ChEBI	CHEBI:10362 Y
Jmol-3D images	Image 1
SMILES O[C@@H]2C/C(=C(/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(\C)CCCC1(C)C)C)C)C)C)C(C)(C)C2)C
InChI InChI=1S/C40H56O/c1-30(18-13-20-32(3)23-25-37-34(5)22-15-27-39(37,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-38-35(6)28-36(41)29-40(38,9)10/h11-14,16-21,23-26,36,41H,15,22,27-29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+/t36-/m1/s1 Y Key: DMASLKHVQRHNES-FKKUPVFPSA-N Y InChI=1/C40H56O/c1-30(18-13-20-32(3)23-25-37-34(5)22-15-27-39(37,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-38-35(6)28-36(41)29-40(38,9)10/h11-14,16-21,23-26,36,41H,15,22,27-29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+/t36-/m1/s1 Key: DMASLKHVQRHNES-FKKUPVFPBQ
Properties
Molecular formula	C40H56O
Molar mass	552.85 g/mol
Melting point	169 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cryptoxanthin is a natural carotenoid pigment. It has been isolated from a variety of sources including the petals and flowers of plants in the genus Physalis, orange rind, papaya, egg yolk, butter, apples, and bovine blood serum.^[1]

Chemistry

In terms of structure, cryptoxanthin is closely related to β-carotene, with only the addition of a hydroxyl group. It is a member of the class of carotenoids known as xanthophylls.

In a pure form, cryptoxanthin is a red crystalline solid with a metallic luster. It is freely soluble in chloroform, benzene, pyridine, and carbon disulfide.^[1]

Biology and medicine

In the human body, cryptoxanthin is converted to vitamin A (retinol) and is, therefore, considered a provitamin A. As with other carotenoids, cryptoxanthin is an antioxidant and may help prevent free radical damage to cells and DNA, as well as stimulate the repair of oxidative damage to DNA.^[2]

Recent findings of an inverse association between β-cryptoxanthin and lung cancer risk in several observational epidemiological studies suggest that β-cryptoxanthin could potentially act as a chemopreventive agent against lung cancer.^[3] On the other hand, in the Grade IV histology group of adult patients diagnosed with malignant glioma, moderate to high intake of cryptoxanthin (for second tertile and for highest tertile compared to lowest tertile, in all cases)) was associated with poorer survival.^[4]

Other uses

Cryptoxanthin is also used as a substance to colour food products (INS number 161c); it is not approved for use in the EU^[5] or USA^{[citation needed]} however it is approved for use in Australia and New Zealand.^[6]

References

1. ^ ^{a b c} Merck Index, 11th Edition, 2612.
2. ^ Lorenzo, Y.; Azqueta, A.; Luna, L.; Bonilla, F.; Dominguez, G.; Collins, A. R. (2008). "The carotenoid  β-cryptoxanthin stimulates the repair of DNA oxidation damage in addition to acting as an antioxidant in human cells". Carcinogenesis 30 (2): 308–14. doi:10.1093/carcin/bgn270. PMID 19056931. 
3. ^ Lian, Fuzhi; Hu, Kang-Quan; Russell, Robert M.; Wang, Xiang-Dong (2006). "β-Cryptoxanthin suppresses the growth of immortalized human bronchial epithelial cells and non-small-cell lung cancer cells and up-regulates retinoic acid receptor b expression". International Journal of Cancer 119 (9): 2084–2089. doi:10.1002/ijc.22111. 
4. ^ Delorenze, Gerald N; McCoy, Lucie; Tsai, Ai-Lin; Quesenberry, Charles P; Rice, Terri; Il'yasova, Dora; Wrensch, Margaret (2010,). "Daily intake of antioxidants in relation to survival among adult patients diagnosed with malignant glioma". BMC Cancer 10: 215. doi:10.1186/1471-2407-10-215. PMC 2880992. PMID 20482871. http://www.biomedcentral.com/1471-2407/10/215. 
5. ^ UK Food Standards Agency: "Current EU approved additives and their E Numbers". http://www.food.gov.uk/safereating/chemsafe/additivesbranch/enumberlist. Retrieved 2011-10-27. 
6. ^ Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". http://www.comlaw.gov.au/Details/F2011C00827. Retrieved 2011-10-27. 

This article about an organic compound is a stub. You can help Wikipedia by expanding it.v · Categories: Carotenoids Tetraterpenes Organic compound stubs Wikimedia Foundation. 2010. Игры ⚽ Поможем написать реферат Masonville, Colorado Beycesultan Look at other dictionaries: cryptoxanthin — [krip΄tō zan′thin, krip΄təzan′thin] n. 〚 CRYPTO + XANTH(O) + IN1〛 a carotenoid pigment, C40H56O, in butter, eggs, and various plants, that can be converted into vitamin A in the body * * * …   Universalium cryptoxanthin — [krip΄tō zan′thin, krip΄təzan′thin] n. [ CRYPTO + XANTH(O) + IN1] a carotenoid pigment, C40H56O, in butter, eggs, and various plants, that can be converted into vitamin A in the body …   English World dictionary cryptoxanthin — noun A xanthophyll pigment (a hydroxy derivative of carotene) that occurs widely in nature. Syn: E161c, food colouring …   Wiktionary cryptoxanthin — (3R) β,β Caroten 3 ol; β caroten 3 ol; carotenoid (specifically, a xanthophyll) yielding 1 mol of vitamin A per mole. Found in many fruits and berries. * * * cryp·to·xan·thin .krip tə zan(t) thən n a red crystalline carotenoid alcohol C40H55OH… …   Medical dictionary cryptoxanthin — cryp·to·xanthin …   English syllables cryptoxanthin — ˌkriptō+ noun Etymology: International Scientific Vocabulary crypt + xanthin : a red crystalline carotenoid alcohol C40H55OH that occurs in many plants (as yellow Indian corn and papaya), in blood serum, and in some animal products (as butter and …   Useful english dictionary Vitamin A — Systematic (IUPAC) name (2E,4E,6E,8E) 3,7 Dimethyl …   Wikipedia Phytochemical — Phytochemicals are plant derived chemical compounds under scientific research for their potential health promoting properties, but with unproved benefits. Phytonutrients refers to plant derived essential nutrients scientifically confirmed as… …   Wikipedia Nutrition — The Nutrition Facts table indicates the amounts of nutrients which experts recommend to limit or consume in adequate amounts. Nutrition (also called nourishment or aliment) is the provision, to cells and organisms, of the materials necessary (in… …   Wikipedia Carotinoid — Als Carotinoide (auch: Karotinoide) bezeichnet man eine umfangreiche Klasse an natürlichen Farbstoffen, die eine gelbe bis rötliche Färbung verursachen. Carotinoide zählen zu den Terpenen. Sie kommen vor allem in den Chromoplasten und Plastiden… …   Deutsch Wikipedia 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”