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MedKoo Cat#: 464290 | Name: Bixin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bixin is an apocarotenoid found in annatto, a natural food coloring obtained from the seeds of the achiote tree (Bixa orellana). Annatto seeds contain about 5% pigments, which consist of 70-80% bixin. Bixin is chemically unstable when isolated and converts via isomerization into trans-bixin (β-bixin), the double-bond isomer. Bixin is soluble in fats and alcohols but insoluble in water. Upon exposure to alkali, the methyl ester is hydrolyzed to produce the dicarboxylic acid norbixin, a water-soluble derivative.

Chemical Structure

Bixin
Bixin
CAS#6983-79-5

Theoretical Analysis

MedKoo Cat#: 464290

Name: Bixin

CAS#: 6983-79-5

Chemical Formula: C25H30O4

Exact Mass: 394.2144

Molecular Weight: 394.51

Elemental Analysis: C, 76.11; H, 7.67; O, 16.22

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 780.00 2 Weeks
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Related CAS #
No Data
Synonym
Bixin;
IUPAC/Chemical Name
(2E,4E,6E,8E,10E,12E,14E,16Z,18E)-20-methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid
InChi Key
RAFGELQLHMBRHD-SLEZCNMESA-N
InChi Code
InChI=1S/C25H30O4/c1-20(12-8-14-22(3)16-18-24(26)27)10-6-7-11-21(2)13-9-15-23(4)17-19-25(28)29-5/h6-19H,1-5H3,(H,26,27)/b7-6+,12-8+,13-9+,18-16+,19-17+,20-10+,21-11+,22-14+,23-15-
SMILES Code
COC(/C=C/C(C)=C\C=C\C(C)=C\C=C\C=C(\C=C\C=C(\C=C\C(O)=O)C)C)=O
Appearance
Solid
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Bixin (BX) possesses anti-inflammatory, anti-tumor and anti-oxidant activities.
In vitro activity:
Treatment of bixin significantly decreased the number of Hep3B cells and morphological study revealed the change in cellular and nuclear morphology that trigger the events of apoptosis confirmed by annexin V/PI staining. Reference: Nutr Cancer. 2018 Aug-Sep;70(6):971-983. https://pubmed.ncbi.nlm.nih.gov/30204479/
In vivo activity:
Diabetic animals developed mechanical allodynia, depressive and anxious-like behavior, increased plasma HbA1, increased LPO, and decreased GSH levels in tissues analyzed. Repeated BIX (bixin)-treatment (at all tested doses) significantly attenuated mechanical allodynia, the depressive (30 and 90 mg/kg) and, anxious-like behaviors (all doses) in diabetic rats, without changing the locomotor performance. BIX (at all tested doses) restored the oxidative parameters in tissues analyzed and reduced the plasma HbA1. Reference: Brain Res. 2021 Jun 6;1767:147557. https://pubmed.ncbi.nlm.nih.gov/34107278/

Preparing Stock Solutions

The following data is based on the product molecular weight 394.51 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Tao S, Yang Y, Li J, Wang H, Ma Y. Bixin Attenuates High-Fat Diet-Caused Liver Steatosis and Inflammatory Injury through Nrf2/PPARα Signals. Oxid Med Cell Longev. 2021 Feb 2;2021:6610124. doi: 10.1155/2021/6610124. PMID: 33603948; PMCID: PMC7872754. 2. Kumar Y, Phaniendra A, Periyasamy L. Bixin Triggers Apoptosis of Human Hep3B Hepatocellular Carcinoma Cells: An Insight to Molecular and IN SILICO Approach. Nutr Cancer. 2018 Aug-Sep;70(6):971-983. doi: 10.1080/01635581.2018.1490445. Epub 2018 Sep 11. PMID: 30204479. 3. Gasparin AT, Rosa ES, Jesus CHA, Guiloski IC, da Silva de Assis HC, Beltrame OC, Dittrich RL, Pacheco SDG, Zanoveli JM, da Cunha JM. Bixin attenuates mechanical allodynia, anxious and depressive-like behaviors associated with experimental diabetes counteracting oxidative stress and glycated hemoglobin. Brain Res. 2021 Jun 6;1767:147557. doi: 10.1016/j.brainres.2021.147557. Epub ahead of print. PMID: 34107278. 4. Yu Y, Wu DM, Li J, Deng SH, Liu T, Zhang T, He M, Zhao YY, Xu Y. Bixin Attenuates Experimental Autoimmune Encephalomyelitis by Suppressing TXNIP/NLRP3 Inflammasome Activity and Activating NRF2 Signaling. Front Immunol. 2020 Dec 9;11:593368. doi: 10.3389/fimmu.2020.593368. PMID: 33362775; PMCID: PMC7756000.
In vitro protocol:
1. Tao S, Yang Y, Li J, Wang H, Ma Y. Bixin Attenuates High-Fat Diet-Caused Liver Steatosis and Inflammatory Injury through Nrf2/PPARα Signals. Oxid Med Cell Longev. 2021 Feb 2;2021:6610124. doi: 10.1155/2021/6610124. PMID: 33603948; PMCID: PMC7872754. 2. Kumar Y, Phaniendra A, Periyasamy L. Bixin Triggers Apoptosis of Human Hep3B Hepatocellular Carcinoma Cells: An Insight to Molecular and IN SILICO Approach. Nutr Cancer. 2018 Aug-Sep;70(6):971-983. doi: 10.1080/01635581.2018.1490445. Epub 2018 Sep 11. PMID: 30204479.
In vivo protocol:
1. Gasparin AT, Rosa ES, Jesus CHA, Guiloski IC, da Silva de Assis HC, Beltrame OC, Dittrich RL, Pacheco SDG, Zanoveli JM, da Cunha JM. Bixin attenuates mechanical allodynia, anxious and depressive-like behaviors associated with experimental diabetes counteracting oxidative stress and glycated hemoglobin. Brain Res. 2021 Jun 6;1767:147557. doi: 10.1016/j.brainres.2021.147557. Epub ahead of print. PMID: 34107278. 2. Yu Y, Wu DM, Li J, Deng SH, Liu T, Zhang T, He M, Zhao YY, Xu Y. Bixin Attenuates Experimental Autoimmune Encephalomyelitis by Suppressing TXNIP/NLRP3 Inflammasome Activity and Activating NRF2 Signaling. Front Immunol. 2020 Dec 9;11:593368. doi: 10.3389/fimmu.2020.593368. PMID: 33362775; PMCID: PMC7756000.
1: Tao S, Yang Y, Li J, Wang H, Ma Y. Bixin Attenuates High-Fat Diet-Caused Liver Steatosis and Inflammatory Injury through Nrf2/PPARα Signals. Oxid Med Cell Longev. 2021 Feb 2;2021:6610124. doi: 10.1155/2021/6610124. PMID: 33603948; PMCID: PMC7872754. 2: Li J, Yang Y, Wei S, Chen L, Xue L, Tian H, Tao S. Corrigendum: Bixin Protects Against Kidney Interstitial Fibrosis Through Promoting STAT6 Degradation. Front Cell Dev Biol. 2021 Jan 29;8:643207. doi: 10.3389/fcell.2020.643207. Erratum for: Front Cell Dev Biol. 2020 Nov 17;8:576988. PMID: 33585473; PMCID: PMC7878666. 3: Buarque FS, Soares CMF, de Souza RL, Pereira MM, Lima ÁS. Development of an ethanolic two-phase system (ETPS) based on polypropylene glycol 2000 + ethylene glycol + ethanol for separation of hydrophobic compounds. Chem Commun (Camb). 2021 Mar 1;57(17):2156-2159. doi: 10.1039/d0cc01542c. PMID: 33523051. 4: Camelo S, Latil M, Veillet S, Dilda PJ, Lafont R. Beyond AREDS Formulations, What Is Next for Intermediate Age-Related Macular Degeneration (iAMD) Treatment? Potential Benefits of Antioxidant and Anti-inflammatory Apocarotenoids as Neuroprotectors. Oxid Med Cell Longev. 2020 Dec 8;2020:4984927. doi: 10.1155/2020/4984927. PMID: 33520083; PMCID: PMC7803142. 5: Naranjo-Durán AM, Quintero-Quiroz J, Rojas-Camargo J, Ciro-Gómez GL. Modified-release of encapsulated bioactive compounds from annatto seeds produced by optimized ionic gelation techniques. Sci Rep. 2021 Jan 14;11(1):1317. doi: 10.1038/s41598-020-80119-1. PMID: 33446706; PMCID: PMC7809057. 6: Li J, Yang Y, Wei S, Chen L, Xue L, Tian H, Tao S. Correction to Bixin Confers Prevention against Ureteral Obstruction-Caused Renal Interstitial Fibrosis through Activation of the Nuclear Factor Erythroid-2-Related Factor2 Pathway in Mice. J Agric Food Chem. 2021 Jan 20;69(2):859. doi: 10.1021/acs.jafc.0c08145. Epub 2021 Jan 7. Erratum for: J Agric Food Chem. 2020 Aug 5;68(31):8321-8329. PMID: 33411527. 7: Yu Y, Wu DM, Li J, Deng SH, Liu T, Zhang T, He M, Zhao YY, Xu Y. Bixin Attenuates Experimental Autoimmune Encephalomyelitis by Suppressing TXNIP/NLRP3 Inflammasome Activity and Activating NRF2 Signaling. Front Immunol. 2020 Dec 9;11:593368. doi: 10.3389/fimmu.2020.593368. PMID: 33362775; PMCID: PMC7756000. 8: Sharma P, Segat A, Kelly AL, Sheehan JJ. Colorants in cheese manufacture: Production, chemistry, interactions, and regulation. Compr Rev Food Sci Food Saf. 2020 Jul;19(4):1220-1242. doi: 10.1111/1541-4337.12519. Epub 2019 Dec 23. PMID: 33337089. 9: Li J, Yang Y, Wei S, Chen L, Xue L, Tian H, Tao S. Bixin Protects Against Kidney Interstitial Fibrosis Through Promoting STAT6 Degradation. Front Cell Dev Biol. 2020 Nov 17;8:576988. doi: 10.3389/fcell.2020.576988. Erratum in: Front Cell Dev Biol. 2021 Jan 29;8:643207. PMID: 33313043; PMCID: PMC7704619. 10: Ma JQ, Zhang YJ, Tian ZK, Liu CM. Bixin attenuates carbon tetrachloride induced oxidative stress, inflammation and fibrosis in kidney by regulating the Nrf2/TLR4/MyD88 and PPAR-γ/TGF-β1/Smad3 pathway. Int Immunopharmacol. 2021 Jan;90:107117. doi: 10.1016/j.intimp.2020.107117. Epub 2020 Nov 6. PMID: 33162346. 11: Gómez-Linton DR, Alavez S, Navarro-Ocaña A, Román-Guerrero A, Pinzón-López L, Pérez-Flores LJ. Achiote (Bixa orellana) Lipophilic Extract, Bixin, and δ-tocotrienol Effects on Lifespan and Stress Resistance in Caenorhabditis elegans. Planta Med. 2020 Oct 29. doi: 10.1055/a-1266-6674. Epub ahead of print. PMID: 33124008. 12: Schmidlin CJ, Rojo de la Vega M, Perer J, Zhang DD, Wondrak GT. Activation of NRF2 by topical apocarotenoid treatment mitigates radiation-induced dermatitis. Redox Biol. 2020 Oct;37:101714. doi: 10.1016/j.redox.2020.101714. Epub 2020 Sep 4. PMID: 32927319; PMCID: PMC7494798. 13: Villacrés-Vallejo J, Aranda-Ventura J, Wallis A, Cagle R, Handy SM, Davis J, Reed E, Zhang S, Strain E, Pava-Ripoll M, Erickson D, Ramachandran P, Ottesen A. Using full chloroplast genomes of 'red' and 'yellow' Bixa orellana (achiote) for kmer based identification and phylogenetic inference. BMC Genomics. 2020 Aug 6;21(1):544. doi: 10.1186/s12864-020-06916-0. PMID: 32762642; PMCID: PMC7430826. 14: Li J, Yang Y, Wei S, Chen L, Xue L, Tian H, Tao S. Bixin Confers Prevention against Ureteral Obstruction-Caused Renal Interstitial Fibrosis through Activation of the Nuclear Factor Erythroid-2-Related Factor2 Pathway in Mice. J Agric Food Chem. 2020 Aug 5;68(31):8321-8329. doi: 10.1021/acs.jafc.0c03674. Epub 2020 Jul 24. Erratum in: J Agric Food Chem. 2021 Jan 20;69(2):859. PMID: 32706966. 15: Shin J, Song MH, Oh JW, Keum YS, Saini RK. Pro-Oxidant Actions of Carotenoids in Triggering Apoptosis of Cancer Cells: A Review of Emerging Evidence. Antioxidants (Basel). 2020 Jun 17;9(6):532. doi: 10.3390/antiox9060532. PMID: 32560478; PMCID: PMC7346220. 16: Quintero Quiroz J, Velazquez V, Corrales-Garcia LL, Torres JD, Delgado E, Ciro G, Rojas J. Use of Plant Proteins as Microencapsulating Agents of Bioactive Compounds Extracted from Annatto Seeds (Bixa orellana L.). Antioxidants (Basel). 2020 Apr 13;9(4):310. doi: 10.3390/antiox9040310. PMID: 32294926; PMCID: PMC7222217. 17: Beni AA, Rodrigues RF, Conte L, Costa IF, Delalibera ÉA, Roehrs M, Rampelotto C, Emanuelli T, Somacal S. Dietary supplementation with annatto food- coloring extracts increases the resistance of human erythrocytes to hemolysis. Nutr Res. 2020 Apr;76:71-81. doi: 10.1016/j.nutres.2020.02.003. Epub 2020 Feb 8. PMID: 32217378. 18: Chazelas E, Deschasaux M, Srour B, Kesse-Guyot E, Julia C, Alles B, Druesne- Pecollo N, Galan P, Hercberg S, Latino-Martel P, Esseddik Y, Szabo F, Slamich P, Gigandet S, Touvier M. Food additives: distribution and co-occurrence in 126,000 food products of the French market. Sci Rep. 2020 Mar 4;10(1):3980. doi: 10.1038/s41598-020-60948-w. PMID: 32132606; PMCID: PMC7055242. 19: Keita H, Dos Santos CBR, Ramos MM, Padilha EC, Serafim RB, Castro AN, Amado JRR, da Silva GM, Ferreira IM, Giuliatti S, Carvalho JCT. Assessment of the hypoglycemic effect of Bixin in alloxan-induced diabetic rats: in vivo and in silico studies. J Biomol Struct Dyn. 2021 Feb;39(3):1017-1028. doi: 10.1080/07391102.2020.1724567. Epub 2020 Feb 13. PMID: 32028848. 20: Suparmi S, de Haan L, Spenkelink A, Louisse J, Beekmann K, Rietjens IMCM. Combining In Vitro Data and Physiologically Based Kinetic Modeling Facilitates Reverse Dosimetry to Define In Vivo Dose-Response Curves for Bixin- and Crocetin-Induced Activation of PPARγ in Humans. Mol Nutr Food Res. 2020 Jan;64(2):e1900880. doi: 10.1002/mnfr.201900880. Epub 2020 Jan 7. PMID: 31846197; PMCID: PMC7003908.