Capsanthin

584.87100

584.87

207-364-1

420NY1J57N

Deep carmine-red needles from petroleum ether

3203001990

57.53000

9.80630

reddish oily liquid

1.012g/cm3

90-100 °C

726.6ºC at 760 mmHg

407.2ºC

1.563

Freely soluble in acetone, chloroform; soluble in methanol, ethanol, ether and benzene; slightly soluble in petroleum ether and carbon disulfide.

2.22E-24mmHg at 25°C

Henry's law constant = 2.9X10-8 cu m-atm/mol at 25 °C (estimated)

Optical rotation (cadmium): +36 deg (chloroform)

3

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Certification of this color additive when used in food is not necessary for the protection of the public health, and therefore batches thereof are exempt from the certification pursuant to section 721(c) of the act. /Paprika/|Certification of this color additive when used in food is not necessary for the protection of the public health, and therefore batches thereof are exempt from the certification pursuant to section 721(c) of the act. /Paprika oleoresin/

LD50 Rat oral 11.25 g/kg bw /Paprika color/

/OTHER TOXICITY INFORMATION/ The toxicity of 14 commercial natural dyes which are widely used as food additives in Japan was studied on Paramecium caudatum. Laccaic acid and capsanthin were found to be very toxic to Paramecium caudatum. Some of the commercially available carminic acid and crocin were also toxic. The inhibitory effect of natural food dyes on leucine aminopeptidase, acid phosphatase and esterase in vitro was proportional to the toxic effect of the dyes on the survival time of Paramecium caudatum. Analyses of the commercial natural food dyes by high performance liquid chromatography failed to identify the toxic components.

Capsanthin has been identified in various species of Capsicum(1,2) as well as Berberis vulgaris(2).

Capsanthin's production and use as an orange food color(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.7X10+7(SRC), determined from a structure estimation method(2), indicates that capsanthin is expected to be immobile in soil(SRC). Volatilization of capsanthin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.9X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Capsanthin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.7X10-18 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation data in soils were not available(SRC, 2011).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.7X10+7(SRC), determined from a structure estimation method(2), indicates that capsanthin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.9X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 12(SRC), from an estimated log Kow of 13(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2011).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), capsanthin, which has an estimated vapor pressure of 4.7X10-18 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase capsanthin may be removed from the air by wet or dry deposition(SRC). Capsanthin contains chromophores that absorb at wavelengths >290 nm(3), and therefore may be susceptible to direct photolysis by sunlight(SRC).

Capsanthin is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Capsanthin contains chromophores that absorb at wavelengths >290 nm(1), and therefore may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 12 was calculated in fish for capsanthin(SRC), using an estimated log Kow of 13(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of capsanthin can be estimated to be 1.7X10+7(SRC). According to a classification scheme(2), this estimated Koc value suggests that capsanthin is expected to be immobile in soil.

The Henry's Law constant for capsanthin is estimated as 2.9X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that capsanthin is expected to be essentially nonvolatile from water surfaces(2). Capsanthin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.7X10-18 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to capsanthin may occur through dermal contact with this compound at workplaces where capsanthin is produced or used. Use data indicate that the general population may be exposed to capsanthin via ingestion of food containing capsanthin as a colorant. (SRC)

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.

/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.

... 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. ...

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/HUMAN EXPOSURE STUDIES/ A low incidence of local reactions in dermatitis patients was observed in skin tests with paprika. Three out of 336 dermatitis patients reacted to paprika powder in a 24 hr patch test. Skin scratch tests with paprika powder were also positive in 59 out of 894 patients susceptible to allergenic agents (atopic patients), but no reactions were seen in 362 normal individual. /Paprika powder/|/CASE REPORTS/ /This report/ describes a 27-year-old subject who developed rhinitis and asthma symptoms 1 year after starting to prepare a certain kind of sausage. He was previously diagnosed as having allergy to coconut, banana, and kiwi and allergic rhinitis to horse, cat, dog, and cow. A positive immediate skin prick test (SPT) for paprika (dry powder of Capsicum annuum [Solanaceae]), coriander (Coriandrum sativum [umbelliferous]), and mace (shell of nutmeg, Myristica fragrans [Myristicaceae]) at a concentration of 10% (wt/vol) was obtained. SPT with other sausage ingredients, mites, pollens, and molds were negative. By EIA, specific /immunoglobulin/ E antibodies to paprika, coriander, and mace were demonstrated. By EIA-inhibition assays, a partial cross-reactivity was found among /immunoglobulin/ E-binding components from paprika and mace. The immunoblot analysis showed two /immunoglobulin/ E-reactive protein bands able to bind to /immunoglobulin/ E from mace of 20 and 40 /kiloDalton/ and two other bands from coriander extract of 50 and 56 /kiloDalton/. No bands were detected from paprika extract. Specific bronchial inhalation challenges showed an immediate asthmatic reaction to extracts from paprika, coriander, and mace with a maximum fall in /forced expiratory vol in 1 sec/ of 26%, 40%, and 31%, respectively, with no late asthmatic reactions. In summary, /the authors/ demonstrate that inhalation of dust from paprika, coriander, and mace can result in an /immunoglobulin/ E-mediated reaction to these spices. In this patient, occupational asthma was due to spices from botanically unrelated species.|/CASE REPORTS/ /Investigators/ reported a case of development of IgE antibodies specific to paprika dust in a person who was previously diagnosed with allergy to coconut, banana and kiwi. However, no cases have been reported after intake of food containing paprika extract.|/ALTERNATIVE and IN VITRO TESTS/ /This study/ investigated whether components of paradicsompaprika have direct antitumor effects or inhibitory effects on cancer growth, using its water extract. /Investigators/ applied collagen gel droplet embedded culture drug sensitivity test (CD-DST) as a screening method, which was developed based on the characteristics of cell culture on collagen matrix. Colon adenocarcinoma cells, epithelial cells of lung cancer, and cervical cancer cells were used. Paradicsompaprika is classified as Capsicum annume L. var. grossum of Solanaceae. It is the first of the Hungarian species that was planted in Japan. It is available as TOMA-P in Japan. TOMA-P contains abundant carotenoids including capsanthin and beta-carotene. Water extract of paradicsompaprika was added to each cell at each concentration, and the mixture was cultured for 24 hr and 7 days. The inhibitory effects against lung cancer and cervical cancer were observed concentration- and time-dependently. The effect was more prominent against lung cancer. The growth of bowel cancer cells was observed after the 7-day exposure of paradicsompaprika at the concentrations below the highest concentration compared to the control. At the highest concentration, the growth inhibition was not different between the 24-hr exposure and the 7-day exposure, which suggests that tumor dormancy was induced. Results of the present study suggest that the water extract of paradicsompaprika can be a candidate of a new anticancer agent. Fat soluble component of paradicsompaprika, capsanthin is regarded as an anti-promoter of cancer. Thus, paradicsompaprika possesses chemopreventive and inhibitory effects on cancer cells.

capsanthin

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