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α-Carotene

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α-Carotene
Skeletal formula
Space-filling model
Names
IUPAC name (6′R)-β,ε-Carotene
Systematic IUPAC name 1,3,3-Trimethyl-2-{(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl}cyclohex-1-ene
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-23,25-28,37H,15-16,24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+Key: ANVAOWXLWRTKGA-JLTXGRSLSA-N
  • InChI=1/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-23,25-28,37H,15-16,24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+Key: ANVAOWXLWRTKGA-JLTXGRSLBQ
SMILES
  • C\C2=C\CCC(C)(C)C2/C=CC(\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
Properties
Chemical formula C40H56
Molar mass 536.873
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

α-Carotene (alpha-carotene) is a form of carotene with a β-ionone ring at one end and an α-ionone ring at the opposite end. It is the second most common form of carotene.

Human physiology

In American and Chinese adults, the mean concentration of serum α-carotene was 4.71 μg/dL. Including 4.22 μg/dL among men and 5.31 μg/dL among women.

Dietary sources

The following vegetables are rich in alpha-carotene:

Research

A 2018 meta-analysis found that both dietary and circulating α-carotene are associated with a lower risk of all-cause mortality. The highest circulating α-carotene category, compared to the lowest, correlated with a 32% reduction in the risk of all-cause mortality, while increased dietary α-carotene intake was linked to a 21% decrease in the risk of all-cause mortality.

References

  1. ^ Li C, Ford ES, Zhao G, Balluz LS, Giles WH, Liu S (March 2011). "Serum α-carotene concentrations and risk of death among US Adults: the Third National Health and Nutrition Examination Survey Follow-up Study". Arch. Intern. Med. 171 (6): 507–15. doi:10.1001/archinternmed.2010.440. PMID 21098341. Archived from the original on November 29, 2010.
  2. Alpha-carotene Linked to Lower Mortality Rates Archived May 13, 2012, at the Wayback Machine, Tufts Health and Nutrition Letter, March 2011
  3. Jayedi A, Rashidy-Pour A, Parohan M, Zargar MS, Shab-Bidar S (2018). "Dietary Antioxidants, Circulating Antioxidant Concentrations, Total Antioxidant Capacity, and Risk of All-Cause Mortality: A Systematic Review and Dose-Response Meta-Analysis of Prospective Observational Studies". Adv Nutr. 9 (6): 701–716. doi:10.1093/advances/nmy040. PMC 6247336. PMID 30239557.
Carotenoids
Carotenes (C40)
Xanthophylls (C40)
Apocarotenoids (C<40)
Vitamin A retinoids (C20)
Retinoid drugs
Vitamins (A11)
Fat
soluble
A
D
E
K
Water
soluble
B
C
Combinations
Types of terpenes and terpenoids (# of isoprene units)
Basic forms:
  • Acyclic (linear, cis and trans forms)
  • Monocyclic (single ring)
  • Bicyclic (2 rings)
  • Iridoids (cyclopentane ring)
  • Iridoid glycosides (iridoids bound to a sugar)
  • Steroids (4 rings)
Hemiterpenoids (1)
Monoterpenes
(C10H16)(2)
Acyclic
Monocyclic
Bicyclic
Monoterpenoids
(2,modified)
Acyclic
Monocyclic
Bicyclic
Sesquiterpenoids (3)
Diterpenoids (4)
Acyclic
Monocyclic
Bicyclic
Tricyclic
Tetracyclic
Resin acids
Sesterterpenoids (5)
  • Geranylfarnesol
Triterpenoids (6)
Steroids
Other
Sesquarterpenes/oids (7)
  • Ferrugicadiol
  • Tetraprenylcurcumene
Tetraterpenoids
(Carotenoids) (8)
Carotenes
Xanthophylls:
Polyterpenoids (many)
Norisoprenoids (modified)
  • 3-oxo-α-ionol
  • 7,8-dihydroionone
Synthesis
Activated isoprene forms
Categories: