Beta-Carotene

CAS# 7235-40-7

Beta-Carotene

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Quality Control of Beta-Carotene

Number of papers citing our products

Chemical structure

Beta-Carotene

3D structure

Chemical Properties of Beta-Carotene

Cas No. 7235-40-7 SDF Download SDF
PubChem ID 5280489 Appearance Powder
Formula C40H56 M.Wt 536.88
Type of Compound Miscellaneous Storage Desiccate at -20°C
Synonyms Provitamin A; Carotaben; beta-Carotene; Lucarotin
Solubility DMSO : 5.5 mg/mL (10.24 mM; Need ultrasonic and warming)
Chemical Name 1,3,3-trimethyl-2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohexene
SMILES CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2=C(CCCC2(C)C)C)C)C
Standard InChIKey OENHQHLEOONYIE-JLTXGRSLSA-N
Standard 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/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Beta-Carotene

The roots of Daucus carota

Biological Activity of Beta-Carotene

DescriptionBeta Carotene is an organic compound and classified as a terpenoid. It is a precursor (inactive form) of vitamin A. Beta-Carotene has antioxidant activity, anti-cancer, and antiapoptotic activities, it has protective effects against gamma-radiation-induced in vivo chromosomal damage. Dietary supplementation of carotenoids may act as moderate hypocholesterolemic agents, secondary to their inhibitory effect on macrophage 3-hydroxy-3-methyl glutaryl coenzyme A (HMGCoA) reductase, the rate limiting enzyme in cholesterol synthesis.
TargetsSOD | Caspase | LDL | HMG-CoA Reductase | MMP(e.g.TIMP) | HIF | GLUT
In vitro

Hypocholesterolemic effect of lycopene and beta-carotene is related to suppression of cholesterol synthesis and augmentation of LDL receptor activity in macrophages.[Pubmed: 9168909 ]

Biochem Biophys Res Commun. 1997 Apr 28;233(3):658-62.

Beta-Carotene and lycopene are derived from plants, and they share similar initial synthetic pathway with cholesterol, which is synthesized in animal but not in plant cells. Thus, we sought to analyze the effect of carotenoids on macrophage cholesterol metabolism, in comparison to the effect of LDL cholesterol and of the cholesterol synthesis inhibitor, fluvastatin. In J-774 A. 1 macrophage cell line, the cellular cholesterol synthesis from [3H]-acetate, but not from [14C] mevalonate, was suppressed by 63% any by 73% following cell incubation with Beta-Carotene or lycopene (10 microM) respectively, in comparison to a 90% and 91% inhibition by LDL (100 micrograms of cholesterol), or by fluvastatin (10 micrograms/ml) respectively. However, unlike LDL derived cholesterol, which also suppresses macrophage LDL receptor activity, lycopene and Beta-Carotene augmented the activity of the macrophage LDL receptor, similarly to the effect of fluvasfatin. In agreement with these in vitro observations, dietary supplementation of tomato's lycopene (60 mg/day) to 6 males for a 3 months period resulted in a significant 14% reduction in their plasma LDL cholesterol concentrations.
CONCLUSIONS:
We thus conclude that dietary supplementation of carotenoids may act as moderate hypocholesterolemic agents, secondary to their inhibitory effect on macrophage 3-hydroxy-3-methyl glutaryl coenzyme A (HMGCoA) reductase, the rate limiting enzyme in cholesterol synthesis.

β-Carotene inhibits neuroblastoma cell invasion and metastasis in vitro and in vivo by decreasing level of hypoxia-inducible factor-1α.[Pubmed: 24746828]

J Nutr Biochem. 2014 Jun;25(6):655-64.

While Beta-Carotene is a vitamin A precursor that has been shown to exert antioxidant and anticancer effects, the anti-metastatic effects of Beta-Carotene on neuroblastoma cells remain poorly understood. The aim of the present study was to investigate the anti-metastatic effects of Beta-Carotene on highly malignant SK-N-BE(2)C neuroblastoma cells in vitro and in vivo.
METHODS AND RESULTS:
Treatment of SK-N-BE(2)C cells with Beta-Carotene was found to attenuate the migratory and invasive capabilities of the cells. In addition, the enzymatic activity and expression of matrix metalloproteinase (MMP)-2 was suppressed following Beta-Carotene treatment under both normoxia and hypoxia. To induce metastasis, immunodeficient nude mice were injected with SK-N-BE(2)C cells via the tail vein in vivo. The incidence of liver metastasis and mean tumor volume in mice that were administered Beta-Carotene was decreased compared to controls. Furthermore, mRNA levels of MMPs, membrane-type (MT) 2 MMP and tissue inhibitors of metalloproteinases in liver tumor tissues were also lower following Beta-Carotene treatment. Level of hypoxia-inducible factor-1α (HIF-1α) and its downstream targets, vascular endothelial growth factor and glucose transporter 1 (GLUT1), were lower both in vitro and in vivo following Beta-Carotene treatment.
CONCLUSIONS:
In conclusion, the present study provides the first evidence that Beta-Carotene may represent an effective chemotherapeutic agent by regulating the invasion and metastasis of neuroblastoma via HIF-1α.

In vivo

Protective effects of chlorogenic acid, curcumin and beta-carotene against gamma-radiation-induced in vivo chromosomal damage.[Pubmed: 7694126]

Mutat Res. 1993 Nov;303(3):109-12.

The mouse bone marrow micronucleus test was carried out to evaluate the possible role of the dietary constituents chlorogenic acid (CGA), curcumin (CR) and Beta-Carotene (BC) in modulating the in vivo chromosomal damage induced by gamma-radiation.
METHODS AND RESULTS:
The results obtained suggest that oral administration of CGA (50, 100 and 200 mg/kg b.w.), CR (5, 10 and 20 mg/kg b.w.) and BC (0.5 and 2.5 mg/kg b.w.) to mice can significantly reduce the frequencies of micronucleated polychromatic erythrocytes (Mn PCEs) induced by whole body exposure to gamma-radiation (1.15 Gy; 0.05 Gy/s). With CGA and CR, this effect was observed after a single administration either 2 h before or immediately after irradiation. However, with BC a 7-day feeding before irradiation was necessary to obtain a significant reduction in the incidence of Mn PCEs.
CONCLUSIONS:
The protective effects of CGA, CR and BC were observed in bone marrow cells sampled 24, 30 and 48 h after exposure to radiation.

Protocol of Beta-Carotene

Cell Research

Inhibitory effect of conjugated dienoic derivatives of linoleic acid and beta-carotene on the in vitro growth of human cancer cells.[Pubmed: 1562989]

Cancer Lett. 1992 Apr 15;63(2):125-33.

The effects of physiologic concentrations of conjugated linoleic acid (CLA) and Beta-Carotene were assessed on human (M21-HPB, malignant melanoma; HT-29, colorectal; MCF-7, breast) cancer cells.
METHODS AND RESULTS:
The incubation of cancer cells with CLA showed significant reductions in proliferation (18-100%) compared to control cultures. M21-HPB and MCF-7 cell mortality was dose- and time-dependent. Beta-Carotene was inhibitory to breast cells only. MCF-7 cells supplemented with CLA incorporated significantly less [3H]leucine (45%), [3H]uridine (63%) and [3H]thymidine (46%) than control cultures. M21-HPB and HT-29 cells supplemented with CLA incorporated less [3H]leucine (25-30%).
CONCLUSIONS:
These in vitro results suggest that CLA and Beta-Carotene may be cytotoxic to human cancer cells in vivo.

Animal Research

Antiapoptotic and antioxidant effects of beta-carotene against methotrexate-induced testicular injury.[Pubmed: 19046577]

Fertil Steril. 2009 Dec;92(6):2028-33.

In each group, 100 tubules were classified as intact, sloughing, atrophic, and degenerated. Caspase-3, a universal effector of apoptosis, was evaluated according to staining in place of coloring as weak, mild, and strong. RESULT(S): To investigate the effect of Beta-Carotene against testicular injury induced by methotrexate (MTX).
METHODS AND RESULTS:
Twenty-eight rats were separated into four groups: control, Beta-Carotene, MTX, and Beta-Carotene + MTX. At the end of the treatment, the animals were killed, and tissue samples were examined via histologic and biochemical methods. In each group, 100 tubules were classified as intact, sloughing, atrophic, and degenerated. Caspase-3, a universal effector of apoptosis, was evaluated according to staining in place of coloring as weak, mild, and strong. In the MTX group, 58.5 + 3.7% of tubules were sloughing, 10.8 + 2.1% of tubules were atrophic, and 2.0 + 0.6% of tubules were degenerative. In the Beta-Carotene + MTX group, the affected tubule number was statistically significantly lower than in the MTX group. The distribution of caspase-3 in the MTX group showed a statistically significant increase, but it decreased in the Beta-Carotene + MTX group. The enzyme activities of catalase (CAT), superoxide dismutase (SOD), and glutathione peroxidase (GP-x) and the level of malondialdehyde (MDA) increased and decreased in parallel.
CONCLUSIONS:
Our results indicate that Beta-Carotene may be useful in decreasing the side effects of chemotherapy, including apoptotic cell death.

Structure Identification
J Food Sci. 2014 Sep;79(9):C1688-94.

β-Carotene as a membrane antioxidant probed by cholesterol-anchored daidzein.[Pubmed: 25103027]


METHODS AND RESULTS:
Beta-Carotene is found to be more effective as an antioxidant in phosphatidylcholine (PC) liposomes when protecting against hydrophilic radicals compared to lipophilic radicals, as measured by the rate of formation of conjugated dienes. Daidzein alone is without effect, but decreases the antioxidative effect of Beta-Carotene for hydrophilic initiation and increases the effect for lipophilic initiation. The newly synthesized 7-cholesterylglycol daidzein has the opposite effect for Beta-Carotene as antioxidant, with a strong enhancement for hydrophilic initiation and a slight decrease for lipophilic initiation.
CONCLUSIONS:
Redistributing Beta-Carotene to membrane surfaces by cholesterol-anchoring of daidzein enhances protection against aqueous radicals significantly at the expense of protection against lipid-derived radicals.

Beta-Carotene Dilution Calculator

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Preparing Stock Solutions of Beta-Carotene

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.8626 mL 9.3131 mL 18.6261 mL 37.2523 mL 46.5653 mL
5 mM 0.3725 mL 1.8626 mL 3.7252 mL 7.4505 mL 9.3131 mL
10 mM 0.1863 mL 0.9313 mL 1.8626 mL 3.7252 mL 4.6565 mL
50 mM 0.0373 mL 0.1863 mL 0.3725 mL 0.745 mL 0.9313 mL
100 mM 0.0186 mL 0.0931 mL 0.1863 mL 0.3725 mL 0.4657 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Beta-Carotene

Beta Carotene is an organic compound and classified as a terpenoid. It is a precursor (inactive form) of vitamin A. Target: Others Beta Carotene is a strongly colored red-orange pigment abundant in plants and fruits.β-Carotene is biosynthesized from geranylgeranyl pyrophosphate. It is a member of the carotenes, which are tetraterpenes, synthesized biochemically from eight isoprene units and thus having 40 carbons. Among this general class of carotenes, β-carotene is distinguished by having beta-rings at both ends of the molecule. Absorption of β-carotene is enhanced if eaten with fats, as carotenes are fat soluble [1, 2].

References:
[1]. Tanumihardjo, S.A., Factors influencing the conversion of carotenoids to retinol: bioavailability to bioconversion to bioefficacy. Int J Vitam Nutr Res, 2002. 72(1): p. 40-5. [2]. Leo, M.A. and C.S. Lieber, Alcohol, vitamin A, and beta-carotene: adverse interactions, including hepatotoxicity and carcinogenicity. Am J Clin Nutr, 1999. 69(6): p. 1071-85.

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References on Beta-Carotene

Antioxidant activity of beta-carotene-related carotenoids in solution.[Pubmed:2779372]

Lipids. 1989 Jul;24(7):659-61.

The effect of the antioxidant activity of Beta-Carotene and related carotenoids on the free radical-oxidation of methyl linoleate in solution was examined by measuring the production of methyl linoleate hydroperoxides. Canthaxanthin and astaxanthin which possess oxo groups at the 4 and 4'-positions in the beta-ionone ring retarded the hydroperoxide formation more efficiently than Beta-Carotene and zeaxanthin which possess no oxo groups. The rates of autocatalytic oxidation of canthaxanthin and astaxanthin were also slower than those of Beta-Carotene and zeaxanthin. These results suggest that canthaxanthin and astaxanthin are more effective antioxidants than Beta-Carotene by stabilizing the trapped radicals.

Protective effects of chlorogenic acid, curcumin and beta-carotene against gamma-radiation-induced in vivo chromosomal damage.[Pubmed:7694126]

Mutat Res. 1993 Nov;303(3):109-12.

The mouse bone marrow micronucleus test was carried out to evaluate the possible role of the dietary constituents chlorogenic acid (CGA), curcumin (CR) and Beta-Carotene (BC) in modulating the in vivo chromosomal damage induced by gamma-radiation. The results obtained suggest that oral administration of CGA (50, 100 and 200 mg/kg b.w.), CR (5, 10 and 20 mg/kg b.w.) and BC (0.5 and 2.5 mg/kg b.w.) to mice can significantly reduce the frequencies of micronucleated polychromatic erythrocytes (Mn PCEs) induced by whole body exposure to gamma-radiation (1.15 Gy; 0.05 Gy/s). With CGA and CR, this effect was observed after a single administration either 2 h before or immediately after irradiation. However, with BC a 7-day feeding before irradiation was necessary to obtain a significant reduction in the incidence of Mn PCEs. The protective effects of CGA, CR and BC were observed in bone marrow cells sampled 24, 30 and 48 h after exposure to radiation.

beta-Carotene as a membrane antioxidant probed by cholesterol-anchored daidzein.[Pubmed:25103027]

J Food Sci. 2014 Sep;79(9):C1688-94.

Beta-Carotene is found to be more effective as an antioxidant in phosphatidylcholine (PC) liposomes when protecting against hydrophilic radicals compared to lipophilic radicals, as measured by the rate of formation of conjugated dienes. Daidzein alone is without effect, but decreases the antioxidative effect of Beta-Carotene for hydrophilic initiation and increases the effect for lipophilic initiation. The newly synthesized 7-cholesterylglycol daidzein has the opposite effect for Beta-Carotene as antioxidant, with a strong enhancement for hydrophilic initiation and a slight decrease for lipophilic initiation. Redistributing Beta-Carotene to membrane surfaces by cholesterol-anchoring of daidzein enhances protection against aqueous radicals significantly at the expense of protection against lipid-derived radicals. Anchoring of daidzein to cholesterol is concluded to be useful as a mechanistic tool for controlling antioxidant distribution in membranes sensitive to radical damage, as supported by quantum mechanical calculation within the density function theory and further supported by fluorescence probes and fluorescence polarization probes.

beta-Carotene inhibits neuroblastoma cell invasion and metastasis in vitro and in vivo by decreasing level of hypoxia-inducible factor-1alpha.[Pubmed:24746828]

J Nutr Biochem. 2014 Jun;25(6):655-64.

Neuroblastoma is the most prevalent extracranial solid tumor in childhood and has poor clinical outcome due to its high potential for metastasis. Consequently, an understanding of the mechanisms that modulate cancer cell invasion, migration and metastasis is important for the development of more effective chemotherapeutic agents. While Beta-Carotene is a vitamin A precursor that has been shown to exert antioxidant and anticancer effects, the anti-metastatic effects of Beta-Carotene on neuroblastoma cells remain poorly understood. The aim of the present study was to investigate the anti-metastatic effects of Beta-Carotene on highly malignant SK-N-BE(2)C neuroblastoma cells in vitro and in vivo. Treatment of SK-N-BE(2)C cells with Beta-Carotene was found to attenuate the migratory and invasive capabilities of the cells. In addition, the enzymatic activity and expression of matrix metalloproteinase (MMP)-2 was suppressed following Beta-Carotene treatment under both normoxia and hypoxia. To induce metastasis, immunodeficient nude mice were injected with SK-N-BE(2)C cells via the tail vein in vivo. The incidence of liver metastasis and mean tumor volume in mice that were administered Beta-Carotene was decreased compared to controls. Furthermore, mRNA levels of MMPs, membrane-type (MT) 2 MMP and tissue inhibitors of metalloproteinases in liver tumor tissues were also lower following Beta-Carotene treatment. Level of hypoxia-inducible factor-1alpha (HIF-1alpha) and its downstream targets, vascular endothelial growth factor and glucose transporter 1 (GLUT1), were lower both in vitro and in vivo following Beta-Carotene treatment. In conclusion, the present study provides the first evidence that Beta-Carotene may represent an effective chemotherapeutic agent by regulating the invasion and metastasis of neuroblastoma via HIF-1alpha.

Hypocholesterolemic effect of lycopene and beta-carotene is related to suppression of cholesterol synthesis and augmentation of LDL receptor activity in macrophages.[Pubmed:9168909]

Biochem Biophys Res Commun. 1997 Apr 28;233(3):658-62.

Beta-Carotene and lycopene are derived from plants, and they share similar initial synthetic pathway with cholesterol, which is synthesized in animal but not in plant cells. Thus, we sought to analyze the effect of carotenoids on macrophage cholesterol metabolism, in comparison to the effect of LDL cholesterol and of the cholesterol synthesis inhibitor, fluvastatin. In J-774 A. 1 macrophage cell line, the cellular cholesterol synthesis from [3H]-acetate, but not from [14C] mevalonate, was suppressed by 63% any by 73% following cell incubation with Beta-Carotene or lycopene (10 microM) respectively, in comparison to a 90% and 91% inhibition by LDL (100 micrograms of cholesterol), or by fluvastatin (10 micrograms/ml) respectively. However, unlike LDL derived cholesterol, which also suppresses macrophage LDL receptor activity, lycopene and Beta-Carotene augmented the activity of the macrophage LDL receptor, similarly to the effect of fluvasfatin. In agreement with these in vitro observations, dietary supplementation of tomato's lycopene (60 mg/day) to 6 males for a 3 months period resulted in a significant 14% reduction in their plasma LDL cholesterol concentrations. We thus conclude that dietary supplementation of carotenoids may act as moderate hypocholesterolemic agents, secondary to their inhibitory effect on macrophage 3-hydroxy-3-methyl glutaryl coenzyme A (HMGCoA) reductase, the rate limiting enzyme in cholesterol synthesis.

Inhibitory effect of conjugated dienoic derivatives of linoleic acid and beta-carotene on the in vitro growth of human cancer cells.[Pubmed:1562989]

Cancer Lett. 1992 Apr 15;63(2):125-33.

The effects of physiologic concentrations of conjugated linoleic acid (CLA) and Beta-Carotene were assessed on human (M21-HPB, malignant melanoma; HT-29, colorectal; MCF-7, breast) cancer cells. The incubation of cancer cells with CLA showed significant reductions in proliferation (18-100%) compared to control cultures. M21-HPB and MCF-7 cell mortality was dose- and time-dependent. Beta-Carotene was inhibitory to breast cells only. MCF-7 cells supplemented with CLA incorporated significantly less [3H]leucine (45%), [3H]uridine (63%) and [3H]thymidine (46%) than control cultures. M21-HPB and HT-29 cells supplemented with CLA incorporated less [3H]leucine (25-30%). These in vitro results suggest that CLA and Beta-Carotene may be cytotoxic to human cancer cells in vivo.

Antiapoptotic and antioxidant effects of beta-carotene against methotrexate-induced testicular injury.[Pubmed:19046577]

Fertil Steril. 2009 Dec;92(6):2028-33.

OBJECTIVE: To investigate the effect of Beta-Carotene against testicular injury induced by methotrexate (MTX). DESIGN: Experimental study. SETTING: Animal and histology laboratory at Inonu University. ANIMAL(S): Twenty-eight Wistar male rats. INTERVENTION(S): Twenty-eight rats were separated into four groups: control, Beta-Carotene, MTX, and Beta-Carotene + MTX. At the end of the treatment, the animals were killed, and tissue samples were examined via histologic and biochemical methods. MAIN OUTCOME MEASURE(S): In each group, 100 tubules were classified as intact, sloughing, atrophic, and degenerated. Caspase-3, a universal effector of apoptosis, was evaluated according to staining in place of coloring as weak, mild, and strong. RESULT(S): In the MTX group, 58.5 + 3.7% of tubules were sloughing, 10.8 + 2.1% of tubules were atrophic, and 2.0 + 0.6% of tubules were degenerative. In the Beta-Carotene + MTX group, the affected tubule number was statistically significantly lower than in the MTX group. The distribution of caspase-3 in the MTX group showed a statistically significant increase, but it decreased in the Beta-Carotene + MTX group. The enzyme activities of catalase (CAT), superoxide dismutase (SOD), and glutathione peroxidase (GP-x) and the level of malondialdehyde (MDA) increased and decreased in parallel. CONCLUSION(S): Our results indicate that Beta-Carotene may be useful in decreasing the side effects of chemotherapy, including apoptotic cell death.

Description

β-Carotene (Provitamin A) is an organic compound and classified as a terpenoid. It is a precursor (inactive form) of vitamin A.

Keywords:

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