Absorption, Distribution and Excretion
The pharmacokinetics of dietary capsanthin were determined in four male volunteers with plasma essentially free of capsanthin at the beginning of the study. They received paprika juice for 1 week, equivalent to three doses of 5.4 umol capsanthin/day, for a total of 16.2 umol/day. The level of capsanthin in plasma reached a plateau (0.10-0.12 umol/L) between day 2 and day 7, and capsanthin was not detectable in plasma by day 16. Capsanthin was distributed in the plasma lipoproteins after 1 week as follows: very low density lipoprotein, 13 +/- 3%; low-density lipoprotein, 44 +/- 3%; and high-density lipoprotein, 43 +/- 3%.
In a /study/ involving the single ingestion of paprika juice (equivalent to 34.2 umol capsanthin) by the same men, the plasma concentration of capsanthin ranged from 0.10 to 0.29 umol/L at 8 hr after ingestion. In contrast, the elevation of the plasma concentration of an acyclic hydrocarbon carotenoid, lycopene, by a single ingestion of tomato soup (equivalent to 186.3 mmol lycopene) in the same subjects was minimal (0.02-0.06 mmol/L). The areas under the plasma concentration-time curves for capsanthin between 0 and 74 hr and for lycopene between 0 and 72 hr were 4.68 +/- 1.22 and 0.81 +/- 0.17 (umol.hr)/L, respectively. The half-lives were calculated to be 20.1 +/- 1.3 hr for capsanthin and 222 +/- 15 hr for lycopene. It was concluded that the clearance of capsanthin is much faster than that of lycopene, although capsanthin is transported into plasma lipoproteins in larger amounts.
The bioavailability of carotenoids from a paprika oleoresin (zeaxanthin, beta- cryptoxanthin, beta-carotene, capsanthin, capsorubin) was assessed in humans. After overnight fasting, nine volunteers ingested a single dose of a paprika oleoresin containing 6.4 mg zeaxanthin, 4.2 mg beta-cryptoxanthin, 6.2 mg beta-carotene, 35.0 mg capsanthin and 2.0 mg capsorubin. At different time points, the carotenoid pattern in the chylomicron fraction of whole blood was analyzed to evaluate carotenoid absorption. From the major carotenoids present in the paprika oleoresin, only zeaxanthin, beta-cryptoxanthin and beta-carotene were detectable in measurable amounts. Although the xanthophylls in paprika oleoresin were mainly present as mono- or diesters, only free zeaxanthin and beta-cryptoxanthin were found. The bioavailability of the pepper-specific carotenoids capsanthin and capsorubin from paprika oleoresin was found to be very low.

---

Metabolism / Metabolites
/A/ study in which rats were gavaged with a mixture of capsaicinoids /was reported/. These substances were extensively metabolized by a variety of metabolic pathways, including 1) hydrolysis of the acid-amide bond and deamination to form vanillylamine, 2) hydroxylation of the vanillyl ring, 3) oxidation of the hydroxyl group in the ring and 4) oxidation of the terminal carbon in the sidechain. /Capsaicinoids/
Later steps of carotenoid biosynthesis catalyzed by cyclase enzymes involve the formation of alpha, beta, and kappa-rings. Examination of the primary structure of lycopene beta-cyclase revealed 55% identity with that of antheraxanthin kappa-cyclase. Recombinant lycopene beta-cyclase afforded only beta-carotene, while recombinant antheraxanthin kappa-cyclase catalyzed the formation of beta-carotene from lycopene as well as the conversion of antheraxanthin into the kappa-carotenoid capsanthin. Since the formation of beta- and kappa-rings involves a transient carotenoid carbocation, this suggests that both cyclases initiate and/or neutralize the incipient carbocation by similar mechanisms. Several amine derivatives protonated at physiological pH were used to examine the molecular basis of this phenomenon. The beta-and kappa-cyclases displayed similar inhibition patterns. Affinity or photoaffinity labeling using p-dimethylamino-benzenediazonium fluoroborate, N,N-dimethyl-2-phenylaziridinium, and nicotine irreversibly inactivated both cyclase enzymes. Photoaffinity labeling using [H(3)]nicotine followed by radiosequence analysis and site-directed mutagenesis revealed the existence of two cyclase domains characterized by the presence of reactive aromatic and carboxylic amino acid residues. /Investigators/ propose that these residues represent the "negative point charges" involved in the coordination of the incipient carotenoid carbocations.

---

Biological Half-Life
... In a /study/ involving the single ingestion of paprika juice (equivalent to 34.2 umol capsanthin) The half-lives /after a single ingestion of paprika juice (equivalent to 34.2 umol capsanthin)/ were calculated to be 20.1 +/- 1.3 hr for capsanthin and 222 +/- 15 hr for lycopene. ...

Non-Human Toxicity Values
LD50 Rat oral 11.25 g/kg bw /Paprika color/

[1]. Red paprika (Capsicum annuum L.) and its main carotenoids, capsanthin and β-carotene, prevent hydrogen peroxide-induced inhibition of gap-junction intercellular communication. Chem Biol Interact. 2016 Jul 25;254:146-55.

[2]. Prevention of N-methylnitrosourea-induced colon carcinogenesis in rats by oxygenated carotenoid capsanthin and capsanthin-rich paprika juice. Proc Soc Exp Biol Med. 2000 Jun;224(2):116-22.

[3]. Purified canola lutein selectively inhibits specific isoforms of mammalian DNA polymerases and reduces inflammatory response. Lipids. 2010 Aug;45(8):713-21.

Capsanthin is a carotenone. It has a role as a plant metabolite.
Capsanthin has been reported in Capsicum annuum, Gallus gallus, and Lilium lancifolium with data available.
See also: Red Pepper (part of).

C40H56O3

584.8709

584.422

465-42-9

5281228

Brown to red liquid

1.0±0.1 g/cm3

726.6±60.0 °C at 760 mmHg

177-178ºC

407.2±29.4 °C

0.0±5.4 mmHg at 25°C

1.563

9.9

2

3

11

43

1310

3

O([H])[C@]1([H])C([H])([H])[C@](C(/C(/[H])=C(\[H])/C(=C(\[H])/C(/[H])=C(\[H])/C(=C(\[H])/C(/[H])=C(\[H])/C(/[H])=C(\C([H])([H])[H])/C(/[H])=C(\[H])/C(/[H])=C(\C([H])([H])[H])/C(/[H])=C(\[H])/C2=C(C([H])([H])[H])C([H])([H])[C@]([H])(C([H])([H])C2(C([H])([H])[H])C([H])([H])[H])O[H])/C([H])([H])[H])/C([H])([H])[H])=O)(C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])C1([H])[H]

VYIRVAXUEZSDNC-RDJLEWNRSA-N

InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-23-36-33(5)25-34(41)26-38(36,6)7)15-11-12-16-30(2)18-14-20-32(4)22-24-37(43)40(10)28-35(42)27-39(40,8)9/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t34-,35+,40+/m1/s1

(2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage.  (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

---

Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

View More

Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

---

Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

View More

Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

---

Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

---

 (Please use freshly prepared in vivo formulations for optimal results.)