beta-Carotene

Not to be confused with beta-keratin.
β-Carotene
Skeletal formula
Space-filling model
Names
IUPAC name
beta,beta-Carotene
Systematic IUPAC name
1,3,3-Trimethyl-2-[3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene
Other names
Betacarotene, β-Carotene,[1] Food Orange 5, Provitamin A, 1,1'-(3,7,12,16-Tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis[2,6,6-trimethylcyclohexene]
Identifiers
7235-40-7 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:17579 YesY
ChEMBL ChEMBL1293 YesY
ChemSpider 4444129 YesY
ECHA InfoCard 100.027.851
EC Number 230-636-6
E number E160a(i) (colours)
PubChem 5280489
UNII 01YAE03M7J YesY
Properties
C40H56
Molar mass 536.89 g·mol−1
Appearance Dark orange crystals
Density 0.941 g/cm3[2]
Melting point 176–184 °C (349–363 °F; 449–457 K)
decomposes[2][3]
Boiling point 654.7 °C (1,210.5 °F; 927.9 K)
at 760 mmHg
Insoluble
Solubility Soluble in CS2, benzene, CHCl3, alcohol
Insoluble in glycerin
Solubility in dichloromethane 4.51 g/kg (20 °C)[4]
Solubility in hexane 0.1 g/L[2]
log P 14.764
Vapor pressure 2.71·10−16 mmHg[2]
1.565[2]
Pharmacology
A11CA02 (WHO) D02BB01 (WHO)
Hazards
Xn[2]
R-phrases R20/21/22, R36/37/38, R44
S-phrases S7, S15, S18, S26, S36
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g., sodium chloride Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
0
0
Flash point 103 °C (217 °F; 376 K)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

β-Carotene is an organic, strongly colored red-orange pigment abundant in plants and fruits. It is a member of the carotenes, which are terpenoids (isoprenoids), synthesized biochemically from eight isoprene units and thus having 40 carbons. Among the carotenes, β-carotene is distinguished by having beta-rings at both ends of the molecule. β-Carotene is biosynthesized from geranylgeranyl pyrophosphate.[5]

β-Carotene is the most common form of carotene in plants. When used as a food coloring, it has the E number E160a.[6]:119 The structure was deduced by Karrer et al. in 1930.[7] In nature, β-carotene is a precursor (inactive form) to vitamin A via the action of beta-carotene 15,15'-monooxygenase.[5]

Isolation of β-carotene from fruits abundant in carotenoids is commonly done using column chromatography. It can also be extracted from the beta-carotene rich algae, Dunaliella salina.[8] The separation of β-carotene from the mixture of other carotenoids is based on the polarity of a compound. β-Carotene is a non-polar compound, so it is separated with a non-polar solvent such as hexane.[9] Being highly conjugated, it is deeply colored, and as a hydrocarbon lacking functional groups, it is very lipophilic.

Provitamin A activity

Plant carotenoids are the primary dietary source of provitamin A worldwide, with β-carotene as the most well-known provitamin A carotenoid. Others include α-carotene and β-cryptoxanthin. Carotenoid absorption is restricted to the duodenum of the small intestine and dependent on class B scavenger receptor (SR-B1) membrane protein, which are also responsible for the absorption of vitamin E (α-tocopherol).[10] One molecule of β-carotene can be cleaved by the intestinal enzyme β,β-carotene 15,15'-monooxygenase into two molecules of vitamin A.[11]

Absorption efficiency is estimated to be between 9 and 22%. The absorption and conversion of carotenoids may depend on the form of β-carotene (e.g., cooked vs. raw vegetables, or in a supplement), the intake of fats and oils at the same time, and the current stores of vitamin A and β-carotene in the body. Researchers list these factors that determine the provitamin A activity of carotenoids:[12]

Symmetric and asymmetric cleavage

In the molecular chain between the two cyclohexyl rings, β-carotene cleaves either symmetrically or asymmetrically. Symmetric cleavage with the enzyme β,β-carotene-15,15'-dioxygenase requires the antioxidant α-tocopherol.[13] This symmetric cleavage gives two equivalent retinal molecules and each retinal molecule further reacts to give retinol (vitamin A) and retinoic acid. β-Carotene is also cleaved into two asymmetric products; the product is β-apocarotenal (8',10',12'). Asymmetric cleavage reduces the level of retinoic acid significantly.[14]

Conversion factors

Since 2001, the US Institute of Medicine uses retinol activity equivalents (RAE) for their Dietary Reference Intakes, defined as follows:[15]

Retinol activity equivalents (RAEs)

1 µg RAE = 1 µg retinol

1 µg RAE = 2 µg all-trans-β-carotene from supplements

1 µg RAE = 12 µg of all-trans-β-carotene from food

1 µg RAE = 24 µg α-carotene or β-cryptoxanthin from food

RAE takes into account carotenoids' variable absorption and conversion to vitamin A by humans better than and replaces the older retinol equivalent (RE) (1 µg RE = 1 µg retinol, 6 µg β-carotene, or 12 µg α-carotene or β-cryptoxanthin).[15] RE was developed 1967 by the United Nations/World Health Organization Food and Agriculture Organization (FAO/WHO).[16]

Another older unit of vitamin A activity is the international unit (IU). Like retinol equivalent, the international unit does not take into account carotenoids' variable absorption and conversion to vitamin A by humans, as well as the more modern retinol activity equivalent. Unfortunately, food and supplement labels still generally use IU, but IU can be converted to the more useful retinol activity equivalent as follows:[15]

International Units

1 µg RAE = 3.33 IU retinol

1 IU retinol = 0.3 μg RAE

1 IU β-carotene from supplements = 0.15 μg RAE

1 IU β-carotene from food = 0.05 μg RAE

1 IU α-carotene or β-cryptoxanthin from food = 0.025 μg RAE1

Dietary sources

Beta-carotene is found in many foods and is sold as a dietary supplement. β-Carotene contributes to the orange color of many different fruits and vegetables. Vietnamese gac (Momordica cochinchinensis Spreng.) and crude palm oil are particularly rich sources, as are yellow and orange fruits, such as cantaloupe, mangoes, pumpkin, and papayas, and orange root vegetables such as carrots and sweet potatoes. The color of β-carotene is masked by chlorophyll in green leaf vegetables such as spinach, kale, sweet potato leaves, and sweet gourd leaves.[17] Vietnamese gac and crude palm oil have the highest content of β-carotene of any known plant sources, 10 times higher than carrots, for example. However, gac is quite rare and unknown outside its native region of Southeast Asia, and crude palm oil is typically processed to remove the carotenoids before sale to improve the color and clarity.[18]

The average daily intake of β-carotene is in the range 2–7 mg, as estimated from a pooled analysis of 500,000 women living in the USA, Canada, and some European countries.[19]

The U.S. Department of Agriculture lists these 10 foods to have the highest β-carotene content per serving.[20]

Item Grams per serving Serving size Milligrams β-carotene per serving Milligrams β-carotene per 100 g
Carrot juice, canned 236 1 cup 22.0 9.3
Pumpkin, canned, without salt 245 1 cup 17.0 6.9
Sweet potato, cooked, baked in skin, without salt 146 1 potato 16.8 11.5
Sweet potato, cooked, boiled, without skin 156 1 potato 14.7 9.4
Spinach, frozen, chopped or leaf, cooked, boiled, drained, without salt 190 1 cup 13.8 7.2
Carrots, cooked, boiled, drained, without salt 156 1 cup 13.0 8.3
Spinach, canned, drained solids 214 1 cup 12.6 5.9
Sweet potato, canned, vacuum pack 255 1 cup 12.2 4.8
Carrots, frozen, cooked, boiled, drained, without salt 146 1 cup 12.0 8.2
Collards, frozen, chopped, cooked, boiled, drained, without salt 170 1 cup 11.6 6.8

Side effects

The most common side effect of excessive β-carotene consumption is carotenodermia, a physically harmless condition that presents as a conspicuous orange skin tint arising from deposition of the carotenoid in the outermost layer of the epidermis.[21] Chronic, high doses of synthetic β-carotene supplements have been associated with a higher rate of lung cancer in smokers. Additionally, supplemental β-carotene may increase the risk of prostate cancer, intracerebral hemorrhage, and cardiovascular and total mortality in people who smoke cigarettes or have a history of high-level exposure to asbestos.[22] β-Carotene has a high tendency to oxidize,[23] more so than most food fats, and may thus to some extent hasten oxidation more than other food colors such as annatto.

Overdose

β-Carotene, a precursor form of vitamin A typical of vegetable sources such as carrots, is selectively converted into retinoids, so it does not cause hypervitaminosis A.

The proportion of carotenoids absorbed decreases as dietary intake increases. Within the intestinal wall (mucosa), β-carotene is partially converted into vitamin A (retinol) by an enzyme, dioxygenase. This mechanism is regulated by the individual's vitamin A status. If the body has enough vitamin A, the conversion of β-carotene decreases. Therefore, β-carotene is a very safe source of vitamin A and high intakes will not lead to hypervitaminosis A. Excess β-carotene is predominantly stored in the fat tissues of the body. The adult's fat stores are often yellow from accumulated carotene, while the infant's fat stores are white. Excessive intake of β-carotene leads to yellowish skin, but this is quickly reversible upon cessation of intake.[24]

Drug interactions

β-Carotene can interact with medication used for lowering cholesterol. Taking them together can lower the effectiveness of these medications and is considered only a moderate interaction.[25] β-Carotene should not be taken with orlistat, a weight-loss medication, as orlistat can reduce the absorption of β-carotene by as much as 30%.[26] Bile acid sequestrants and proton-pump inhibitors can also decrease absorption of β-carotene.[27] Consuming alcohol with β-carotene can decrease its ability to convert to retinol and could possibly result in hepatotoxicity.[28]

β-Carotene and lung cancer in smokers

Chronic high doses of β-carotene supplementation increases the probability of lung cancer in cigarette smokers.[29] The effect is specific to supplementation dose as no lung damage has been detected in those who are exposed to cigarette smoke and who ingest a physiologic dose of β-carotene (6 mg), in contrast to high pharmacologic dose (30 mg). Therefore, the oncology from β-carotene is based on both cigarette smoke and high daily doses of β-carotene.[30]

Another β-carotene breakdown product suspected of causing cancer at high dose is trans-β-apo-8'-carotenal (common apocarotenal), which has been found in one study to be mutagenic and genotoxic in cell cultures which do not respond to β-carotene itself.[31]

Research

Medical authorities generally recommend obtaining beta-carotene from food rather than dietary supplements.[32] Research is insufficient to determine whether a minimum level of beta-carotene consumption is necessary for human health and to identify what problems might arise from insufficient beta-carotene intake,[33] although strict vegetarians rely on pro-vitamin A carotenoids to meet their vitamin A requirements. Use of beta-carotene to treat or prevent some diseases has been studied.

Cancer

A 2010 systemic meta review concluded that supplementation with β-carotene does not appear to decrease the risk of cancer overall, nor specific cancers including: pancreatic, colorectal, prostate, breast, melanoma, or skin cancer generally.[34] High levels of β-carotene may increase the risk of lung cancer in current and former smokers.[35] This is likely because beta-carotene is unstable in cigarette smoke-exposed lungs where it forms oxidized metabolites that can induce carcinogen-bioactivating enzymes.[36] Results are not clear for thyroid cancer.[37] In a single, small clinical study published in 1989, natural beta-carotene appeared to reduce premalignant gastric lesions.[33]:177

Cataract

A Cochrane review looked at supplementation of β-carotene, vitamin C, and vitamin E, independently and combined, on people to examine differences in risk of cataract, cataract extraction, progression of cataract, and slowing the loss of visual acuity. These studies found no evidence of any protective effects afforded by β-carotene supplementation on preventing and slowing age-related cataract.[38]

See also

References

  1. ↑ "SciFinder - CAS Registry Number 7235-40-7". Retrieved Oct 21, 2009.
  2. 1 2 3 4 5 6 "beta-Carotene msds". http://wenku.baidu.com. Retrieved 2014-05-27. External link in |website= (help)
  3. 1 2 Sigma-Aldrich Co., β-Carotene. Retrieved on 2014-05-27.
  4. ↑ http://chemister.ru/Database/properties-en.php?dbid=1&id=3518
  5. 1 2 Susan D. Van Arnum (1998), "Vitamin A", Kirk-Othmer Encyclopedia of Chemical Technology (45), New York: John Wiley, pp. 99–107, doi:10.1002/0471238961.2209200101181421.a01, ISBN 0-471-23896-1
  6. ↑ Milne, George W. A. (2005). Gardner's commercially important chemicals: synonyms, trade names, and properties. New York: Wiley-Interscience. ISBN 0-471-73518-3.
  7. ↑ P. Karrer; A. Helfenstein; H. Wehrli; A. Wettstein (1930). "Pflanzenfarbstoffe XXV. Über die Konstitution des Lycopins und Carotins". Helvetica Chimica Acta. 13 (5): 1084–1099. doi:10.1002/hlca.19300130532.
  8. ↑ States4439629 United States expired 4439629, Rudolf Rüegg, "Extraction Process for Beta-Carotene", published March 27, 1984, assigned to Hoffmann-La Roche Inc.
  9. ↑ Mercadante, A.Z.; Steck, A.; Pfander, H. (1999). "Carotenoids from Guava (Psidium guajava L.): Isolation and Structure Elucidation". J. Agric. Food Chem. 47 (1): 145–151. doi:10.1021/jf980405r. PMID 10563863.
  10. ↑ van Bennekum, A; Werder, Moritz; Thuahnai, Stephen T.; Han, Chang-Hoon; Duong, Phu; Williams, David L.; Wettstein, Philipp; Schulthess, Georg; et al. (2005). "Class B scavenger receptor-mediated intestinal absorption of dietary β-carotene and cholesterol". Biochemistry. 44 (11): 4517–25. doi:10.1021/bi0484320. PMID 15766282.
  11. ↑ Biesalski HK, Chichili GR, Frank J, von Lintig J, Nohr D (2007). "Conversion of β-carotene to retinal pigment". Vitamins and hormones. Vitamins & Hormones. 75: 117–30. doi:10.1016/S0083-6729(06)75005-1. ISBN 978-0-12-709875-3. PMID 17368314.
  12. ↑ Tanumihardjo, SA (2002). "Factors influencing the conversion of carotenoids to retinol: bioavailability to bioconversion to bioefficacy". Int J Vit Nutr Res. 72 (1): 40–5. doi:10.1024/0300-9831.72.1.40. PMID 11887751.
  13. ↑ Lakshman, MR (2004). "Alpha and omega of carotenoid cleavage". J Nutr. 134 (2): 241S–245S. PMID 14704327.
  14. ↑ Kiefer, C.; Hessel, S.; Lampert, S.M.; Vogt, K.; Lederer, M.O.; Breithaupt, D.E.; von Lintig, J. (2001). "Identification and Characterization of a Mammalian Enzyme Catalyzing the Asymmetric Oxidative Cleavage of Provitamin A". The Journal of Biological Chemistry. 276 (17): 14110–14116. doi:10.1074/jbc.M011510200 (inactive 2015-04-15). PMID 11278918.
  15. 1 2 3 Dietary Reference Intakes for Vitamin A, Vitamin K, Arsenic, Boron, Chromium, Copper, Iodine, Iron, Manganese, Molybdenum, Nickel, Silicon, Vanadium and Zinc. (free download): National Academy Press. 2001.
  16. ↑ Food and Agriculture Organization/World Health Organization (1967). Requirement of Vitamin A, Thiamine, Riboflavin and Niacin. FAO Food and Nutrition Series B. Rome.
  17. ↑ Kidmose, U; Edelenbos M; Christensen LP; Hegelund E. (2005). "Chromatographic determination of changes in pigments in spinach (Spinacia oleracea L.) during processing.". J Chromatogr Sci. 46 (9): 466–72. PMID 16212792.
  18. ↑ A.N. Mustapa, Z.A. Manan, C.Y. Mohd Azizi, W.B. Setianto, A.K. Mohd Omar, (2011) Extraction of b-carotenes from palm oil mesocarp using sub-critical R134a. Food Chemistry, 125, 262-267.
  19. ↑ Koushik A, Hunter DJ, Spiegelman D, Anderson KE, Buring JE, Freudenheim JL, Goldbohm RA, Hankinson SE, Larsson SC, Leitzmann M, Marshall JR, McCullough ML, Miller AB, Rodriguez C, Rohan TE, Ross JA, Schatzkin A, Schouten LJ, Willett WC, Wolk A, Zhang SM, Smith-Warner SA (2006). "Intake of the major carotenoids and the risk of epithelial ovarian cancer in a pooled analysis of 10 cohort studies". Int J Cancer. 119 (9): 2148–54. doi:10.1002/ijc.22076. PMID 16823847.
  20. ↑ "USDA National Nutrient Database for Standard Reference, Release 21". Retrieved 2009-07-24.
  21. ↑ Stahl W; Heinrich U; Jungmann H; et al. (1998). "Increased Dermal Carotenoid Levels Assessed by Noninvasive Reflection Spectrophotometry Correlate with Serum Levels in Women Ingesting Betatene". Journal of Nutrition. 128 (5): 903–7. PMID 9567001.
  22. ↑ Beta-carotene, MedlinePlus
  23. ↑ Hurst, J. S.; Saini, M. K.; Jin, G. F.; Awasthi, Y. C.; Van Kuijk, F. J. G. M. (2005). "Toxicity of oxidized β-carotene to cultured human cells". Experimental Eye Research. 81 (2): 239–243. doi:10.1016/j.exer.2005.04.002. PMID 15967438.
  24. ↑ "Beta-carotene". DSM.
  25. ↑ Web MD. "Beta-Carotene Interactions". Retrieved 28 May 2012.
  26. ↑ University of Maryland Medical Center. "Possible Interactions with Beta-Carotene". Retrieved 29 May 2012.
  27. ↑ Meschino Health. "Comprehensive Guide to Beta-Carotene". Retrieved 29 May 2012.
  28. ↑ Leo, M. A.; Lieber, C. S. (1999). "Alcohol, vitamin A, and beta-carotene: Adverse interactions, including hepatotoxicity and carcinogenicity". The American Journal of Clinical Nutrition. 69 (6): 1071–1085. PMID 10357725.
  29. ↑ Tanvetyanon T, Bepler G (July 2008). "Beta-carotene in multivitamins and the possible risk of lung cancer among smokers versus former smokers: a meta-analysis and evaluation of national brands". Cancer. 113 (1): 150–7. doi:10.1002/cncr.23527. PMID 18429004.
  30. ↑ Russel, R.M. (2002). "Beta-carotene and lung cancer". Pure Appl. Chem. 74 (8): 1461–1467. doi:10.1351/pac200274081461.
  31. ↑ Alija AJ, Bresgen N, Sommerburg O, Siems W, Eckl PM (2004). "Cytotoxic and genotoxic effects of β-carotene breakdown products on primary rat hepatocytes". Carcinogenesis. 25 (5): 827–31. doi:10.1093/carcin/bgh056. PMID 14688018.
  32. ↑ WebMD. "Find a Vitamin or Supplement – Beta Carotene". Retrieved 29 May 2012.
  33. 1 2 Stargrove, Mitchell (2007-12-20). , Herb, nutrient, and drug interactions : clinical implications and therapeutic strategies (1 ed.). Mosby. ISBN 978-0323029643.
  34. ↑ Druesne-Pecollo, N; Latino-Martel, P; Norat, T; Barrandon, E; Bertrais, S; Galan, P; Hercberg, S (Jul 1, 2010). "Beta-carotene supplementation and cancer risk: a systematic review and metaanalysis of randomized controlled trials.". International Journal of Cancer. Journal International Du Cancer. 127 (1): 172–84. doi:10.1002/ijc.25008. PMID 19876916.
  35. ↑ Misotti, AM; Gnagnarella, P (2013). "Vitamin supplement consumption and breast cancer risk: a review". Ecancermedicalscience. 7: 365. doi:10.3332/ecancer.2013.365. PMC 3805144Freely accessible. PMID 24171049.
  36. ↑ Russell, RM (January 2004). "The enigma of beta-carotene in carcinogenesis: what can be learned from animal studies.". The Journal of Nutrition. 134 (1): 262S–268S. PMID 14704331.
  37. ↑ Zhang, LR; Sawka, AM; Adams, L; Hatfield, N; Hung, RJ (Mar 2013). "Vitamin and mineral supplements and thyroid cancer: a systematic review.". European Journal of Cancer Prevention. 22 (2): 158–68. doi:10.1097/cej.0b013e32835849b0. PMID 22926510.
  38. ↑ Mathew MC, Ervin AM, Tao J, Davis RM (2012). "Routine Antioxidant vitamin supplementation for preventing and slowing the progression of age-related cataract". Cochrane Database Syst Rev. 6: CD004567. doi:10.1002/14651858.CD004567.pub2. PMID 22696344.
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