Chemistry:Beta-Carotene

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Short description: Chemical compound


β-Carotene
Skeletal formula
Space-filling model
Β-Carotene powder.jpg
Names
IUPAC name
all-trans-β,β-Carotene
Preferred IUPAC name
1,1′-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-Tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl]bis(2,6,6-trimethylcyclohex-1-ene)
Other names
Betacarotene (INN), β-Carotene,[1] Food Orange 5, Provitamin A
Identifiers
3D model (JSmol)
3DMet
1917416
ChEBI
ChEMBL
ChemSpider
EC Number
  • 230-636-6
KEGG
UNII
Properties
C40H56
Molar mass 536.888 g·mol−1
Appearance Dark orange crystals
Density 1.00 g/cm3[2]
Melting point 183 °C (361 °F; 456 K)
decomposes[4]
Boiling point 654.7 °C (1,210.5 °F; 927.9 K)
at 760 mmHg (101324 Pa)
Insoluble
Solubility Soluble in CS2, benzene, CHCl3, ethanol
Insoluble in glycerin
Solubility in dichloromethane 4.51 g/kg (20 °C)[3] = 5.98 g/L (given BCM density of 1.3266 g/cm3 at 20°C)
Solubility in hexane 0.1 g/L
log P 14.764
Vapor pressure 2.71·10−16 mmHg
1.565
Pharmacology
1=ATC code }} A11CA02 (WHO) D02BB01 (WHO)
Hazards
GHS pictograms GHS07: Harmful
GHS Signal word Warning
H315, H319, H412
P264, P273, P280, P302+352, P305+351+338, P321, P332+313, P337+313, P362, P501
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
0
0
Flash point 103 °C (217 °F; 376 K)[4]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is ☑Y☒N ?)
Infobox references
Tracking categories (test):

β-Carotene is an organic, strongly coloured red-orange pigment originating and abundant in fungi,[5] plants, fruits and present also in animals. 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.[6]. β-Carotene exists in various geometric isomer forms ranging from the most prominant form in fauna and flora all-trans-β-carotene besides mono-cis-isomers like 13-cis-β-carotene and 9-cis-β-carotene [7].

In some Mucoralean fungi, β-Carotene is a precursor to the synthesis of trisporic acid.[5]

β-Carotene is the most common form of carotene in plants. When used as a food coloring, it has the E number E160a.[8]:119 The structure was deduced by Karrer et al. in 1930.[9] In nature, β-carotene is a precursor (inactive form) to vitamin A via the action of beta-carotene 15,15'-monooxygenase.[6]

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.[10] 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.[11] 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 best-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 is also responsible for the absorption of vitamin E (α-tocopherol).[12] One molecule of β-carotene can be cleaved by the intestinal enzyme β,β-carotene 15,15'-monooxygenase into two molecules of vitamin A.[13]

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:[14]

  • Species of carotene
  • Molecular linkage
  • Amount in the meal
  • Matrix properties
  • Effectors
  • Nutrient status
  • Genetics
  • Host specificity
  • Interactions between factors

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 an antioxidant such as α-tocopherol.[15] 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.[16]

Conversion factors

Since 2001, the US Institute of Medicine uses retinol activity equivalents (RAE) for their Dietary Reference Intakes, defined as follows:[17]

Retinol activity equivalents (RAEs)

1 µg RE = 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).[17] RE was developed 1967 by the United Nations/World Health Organization Food and Agriculture Organization (FAO/WHO).[18]

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:[17]

International Units

  • 1 µg RAE = 3.33 IU retinol
  • 1 IU retinol = 0.3 μg RAE
  • 1 IU β-carotene from supplements = 0.3 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.[19] 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.[20]

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 US, Canada, and some European countries.[21]

The U.S. Department of Agriculture lists these 10 foods to have the highest β-carotene content per serving.[22]

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

Excess β-carotene is predominantly stored in the fat tissues of the body. 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.[23] Adults' fat stores are often yellow from accumulated carotenoids, including β-carotene, while infants' fat stores are white. Carotenodermia is quickly reversible upon cessation of excessive intakes.[24]

Excessive intakes and vitamin A toxicity

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 considered a safe source of vitamin A and high intakes will not lead to hypervitaminosis A.[citation needed]

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 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]

Increases in lung cancer may be due to the tendency of β-carotene to oxidize,[31] and may hasten oxidation more than other food colors such as annatto. A 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.[32]

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.[33]

Research

Medical authorities generally recommend obtaining beta-carotene from food rather than dietary supplements.[34] 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,[35] 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.[citation needed]

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.[36] High levels of β-carotene may increase the risk of lung cancer in current and former smokers.[37] This is likely because beta-carotene is unstable in cigarette smoke-exposed lungs where it forms oxidized metabolites that can induce carcinogen-bioactivating enzymes.[38] Results are not clear for thyroid cancer.[39] In a single, small clinical study published in 1989, natural beta-carotene appeared to reduce premalignant gastric lesions.[35]: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.[40] A second meta-analysis compiled data from studies that measured diet-derived serum beta-carotene and reported a not statistically significant 10% decrease in cataract risk.[41]

Nanotechnology

Dispersed β-carotene molecules can be encapsulated into carbon nanotubes enhancing their optical properties.[42] Efficient energy transfer occurs between the encapsulated dye and nanotube — light is absorbed by the dye and without significant loss is transferred to the nanotube. Encapsulation increases chemical and thermal stability of β-carotene molecules; it also allows their isolation and individual characterization.[43]

See also

References

  1. ↑ "SciFinder – CAS Registry Number 7235-40-7". https://scifinder.cas.org. 
  2. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named r1
  3. ↑ β-carotene. chemister.ru
  4. ↑ 4.0 4.1 Sigma-Aldrich Co., β-Carotene. Retrieved on 2014-05-27.
  5. ↑ 5.0 5.1 Lee, Soo Chan; Ristaino, Jean B.; Heitman, Joseph (13 December 2012). "Parallels in Intercellular Communication in Oomycete and Fungal Pathogens of Plants and Humans". PLOS Pathogens 8 (12): e1003028. doi:10.1371/journal.ppat.1003028. PMID 23271965. 
  6. ↑ 6.0 6.1 Van Arnum, Susan D. (1998), "Vitamin A", Kirk-Othmer Encyclopedia of Chemical Technology, New York: John Wiley, pp. 99–107, doi:10.1002/0471238961.2209200101181421.a01, ISBN 978-0-471-23896-6 
  7. ↑ "From carotenoid intake to carotenoid blood and tissue concentrations - implications for dietary intake recommendations". Nutr. Rev. 79 (5): 544-573. April 2021. doi:10.1093/nutrit/nuaa008. PMID 32766681. 
  8. ↑ Milne, George W. A. (2005). Gardner's commercially important chemicals: synonyms, trade names, and properties. New York: Wiley-Interscience. ISBN 978-0-471-73518-2. 
  9. ↑ "Pflanzenfarbstoffe XXV. Über die Konstitution des Lycopins und Carotins". Helvetica Chimica Acta 13 (5): 1084–1099. 1930. doi:10.1002/hlca.19300130532. 
  10. ↑ Rüegg, Rudolf, "Extraction Process for Beta-Carotene", States4439629 United States patent expired 4439629, published March 27, 1984, assigned to Hoffmann-La Roche Inc.
  11. ↑ "Carotenoids from guava (Psidium guajava l.): isolation and structure elucidation". Journal of Agricultural and Food Chemistry 47 (1): 145–51. January 1999. doi:10.1021/jf980405r. PMID 10563863. 
  12. ↑ "Class B scavenger receptor-mediated intestinal absorption of dietary beta-carotene and cholesterol". Biochemistry 44 (11): 4517–25. March 2005. doi:10.1021/bi0484320. PMID 15766282. 
  13. ↑ "Conversion of β‐Carotene to Retinal Pigment". Conversion of β-carotene to retinal pigment. Vitamins & Hormones. 75. 2007. pp. 117–30. doi:10.1016/S0083-6729(06)75005-1. ISBN 978-0-12-709875-3. 
  14. ↑ "Factors influencing the conversion of carotenoids to retinol: bioavailability to bioconversion to bioefficacy". International Journal for Vitamin and Nutrition Research 72 (1): 40–5. January 2002. doi:10.1024/0300-9831.72.1.40. PMID 11887751. 
  15. ↑ "Alpha and omega of carotenoid cleavage". The Journal of Nutrition 134 (1): 241S–245S. January 2004. doi:10.1093/jn/134.1.241S. PMID 14704327. 
  16. ↑ "Identification and characterization of a mammalian enzyme catalyzing the asymmetric oxidative cleavage of provitamin A". The Journal of Biological Chemistry 276 (17): 14110–6. April 2001. doi:10.1074/jbc.M011510200. PMID 11278918. 
  17. ↑ 17.0 17.1 17.2 Institute of Medicine (US) Panel on Micronutrients (2001). 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. doi:10.17226/10026. ISBN 978-0-309-07279-3. 
  18. ↑ Food and Agriculture Organization/World Health Organization (1967). Requirement of Vitamin A, Thiamine, Riboflavin and Niacin. FAO Food and Nutrition Series B. Rome. 
  19. ↑ "Chromatographic determination of changes in pigments in spinach (Spinacia oleracea L.) during processing". Journal of Chromatographic Science 43 (9): 466–72. October 2005. doi:10.1093/chromsci/43.9.466. PMID 16212792. 
  20. ↑ "Extraction of β-carotenes from palm oil mesocarp using sub-critical R134a". Food Chemistry 125: 262–267. 2011. doi:10.1016/j.foodchem.2010.08.042. http://www.cheme.utm.my/cheme/images/Research/Journal_Articles/2011/journal-16-2011.pdf. 
  21. ↑ "Intake of the major carotenoids and the risk of epithelial ovarian cancer in a pooled analysis of 10 cohort studies". International Journal of Cancer 119 (9): 2148–54. November 2006. doi:10.1002/ijc.22076. PMID 16823847. 
  22. ↑ "USDA National Nutrient Database for Standard Reference, Release 21". http://www.ars.usda.gov/Services/docs.htm?docid=17477. 
  23. ↑ "Increased dermal carotenoid levels assessed by noninvasive reflection spectrophotometry correlate with serum levels in women ingesting Betatene". The Journal of Nutrition 128 (5): 903–7. May 1998. doi:10.1093/jn/128.5.903. PMID 9567001. 
  24. ↑ "Beta-carotene". DSM. http://www.dsm.com/en_US/html/dnpna/hnh_caro_bc.htm. 
  25. ↑ Web MD. "Beta-Carotene Interactions". http://www.webmd.com/vitamins-supplements/ingredientmono-999-BETA-CAROTENE.aspx?activeIngredientId=999&activeIngredientName=BETA-CAROTENE. 
  26. ↑ University of Maryland Medical Center. "Possible Interactions with Beta-Carotene". http://www.umm.edu/altmed/articles/beta-carotene-000941.htm. 
  27. ↑ Meschino Health. "Comprehensive Guide to Beta-Carotene". http://www.meschinohealth.com/books/beta_carotene. 
  28. ↑ "Alcohol, vitamin A, and beta-carotene: adverse interactions, including hepatotoxicity and carcinogenicity". The American Journal of Clinical Nutrition 69 (6): 1071–85. June 1999. doi:10.1093/ajcn/69.6.1071. PMID 10357725. 
  29. ↑ "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. July 2008. 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. ↑ "Toxicity of oxidized beta-carotene to cultured human cells". Experimental Eye Research 81 (2): 239–43. August 2005. doi:10.1016/j.exer.2005.04.002. PMID 15967438. 
  32. ↑ "Cytotoxic and genotoxic effects of beta-carotene breakdown products on primary rat hepatocytes". Carcinogenesis 25 (5): 827–31. May 2004. doi:10.1093/carcin/bgh056. PMID 14688018. 
  33. ↑ Beta-carotene, MedlinePlus
  34. ↑ WebMD. "Find a Vitamin or Supplement – Beta Carotene". http://www.webmd.com/vitamins-supplements/ingredientmono-999-BETA-CAROTENE.aspx?activeIngredientId=999&activeIngredientName=BETA-CAROTENE. 
  35. ↑ 35.0 35.1 Stargrove, Mitchell (2007-12-20). Herb, nutrient, and drug interactions : clinical implications and therapeutic strategies (1 ed.). Mosby. ISBN 978-0323029643. 
  36. ↑ "Beta-carotene supplementation and cancer risk: a systematic review and metaanalysis of randomized controlled trials". International Journal of Cancer 127 (1): 172–84. July 2010. doi:10.1002/ijc.25008. PMID 19876916. 
  37. ↑ "Vitamin supplement consumption and breast cancer risk: a review". ecancermedicalscience 7: 365. October 2013. doi:10.3332/ecancer.2013.365. PMID 24171049. 
  38. ↑ "The enigma of beta-carotene in carcinogenesis: what can be learned from animal studies". The Journal of Nutrition 134 (1): 262S–268S. January 2004. doi:10.1093/jn/134.1.262S. PMID 14704331. 
  39. ↑ "Vitamin and mineral supplements and thyroid cancer: a systematic review". European Journal of Cancer Prevention 22 (2): 158–68. March 2013. doi:10.1097/cej.0b013e32835849b0. PMID 22926510. 
  40. ↑ "Antioxidant vitamin supplementation for preventing and slowing the progression of age-related cataract". The Cochrane Database of Systematic Reviews 6 (6): CD004567. June 2012. doi:10.1002/14651858.CD004567.pub2. PMID 22696344. 
  41. ↑ "Association of blood antioxidants and vitamins with risk of age-related cataract: a meta-analysis of observational studies". The American Journal of Clinical Nutrition 98 (3): 778–86. September 2013. doi:10.3945/ajcn.112.053835. PMID 23842458. 
  42. ↑ "Light-Harvesting Function of β-Carotene Inside Carbon Nanotubes". Phys. Rev. B 74 (15): 155420. 2006. doi:10.1103/PhysRevB.74.155420. Bibcode: 2006PhRvB..74o5420Y. http://pubman.nims.go.jp/pubman/item/escidoc:1587358:2/component/escidoc:1597178/Prb155420.pdf. 
  43. ↑ "Vibrational Analysis of Organic Molecules Encapsulated in Carbon Nanotubes by Tip-Enhanced Raman Spectroscopy". Jpn. J. Appl. Phys. 45 (12): 9286–9289. 2006. doi:10.1143/JJAP.45.9286. Bibcode: 2006JaJAP..45.9286S. 

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