Γ-Tocotrienol

γ-Tocotrienol
Names

Preferred IUPAC name (2R)-2,7,8-Trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol
Identifiers
CAS Number	14101-61-2^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:33277^Y
ChEMBL	ChEMBL120697^Y
ChemSpider	4445514^Y
ECHA InfoCard	100.131.059
MeSH	gamma-tocotrienol
PubChem CID	5282349
UNII	185QAE24TR^Y
CompTox Dashboard (EPA)	DTXSID101019984
InChI InChI=1S/C28H42O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h11,13,15,19,29H,8-10,12,14,16-18H2,1-7H3/b21-13+,22-15+/t28-/m1/s1 Key: OTXNTMVVOOBZCV-WAZJVIJMSA-N
SMILES CC1=C(C=C2CC[C@@](OC2=C1C)(C)CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C)O
Properties
Chemical formula	C₂₈H₄₂O₂
Molar mass	410.63188 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

γ-Tocotrienol is one of the four types of tocotrienol, a type of vitamin E. ^[1]^[2]

Vitamin E exists in nature in eight forms, each of which consists of a head section joined to either a saturated (phytyl) or an unsaturated (farnesyl) tail. The four compounds with the saturated tails are the tocopherols, and the four compounds with the unsaturated tails are the tocotrienols. There are four unique dihydrocoumarin head sections, distinguished by one of four substitution patterns and designated as α, β, γ, or δ. The alpha- forms are distinguished by their three substituted methyl groups and the delta- forms by their one substituted methyl group. The beta- and gamma- forms both have two substituted methyl groups, although at different structural positions (5,8-dimethyl and 7,8-dimethyl, respectively), making both beta / gamma tocotrienol as well as the beta / gamma tocopherol pairs of stereoisomer.^[1]

References

^ ^a ^b Barrie T, Watson RR, Preedy VR, eds. (2013). Tocotrienols: Vitamin E Beyond Tocopherols (2nd ed.). Boca Raton: CRC Press. ISBN 9781439884416.
^ Komiyama K, Iizuka K, Yamaoka M, Watanabe H, Tsuchiya N, Umezawa I (May 1989). "Studies on the biological activity of tocotrienols". Chemical & Pharmaceutical Bulletin. 37 (5): 1369–71. doi:10.1248/cpb.37.1369. PMID 2630104.

Vitamins (A11)

Fat
soluble

A	α-Carotene β-Carotene Retinol^# Tretinoin^#
D	D₂ Ergosterol Ergocalciferol^# D₃ 7-Dehydrocholesterol Previtamin D₃ Cholecalciferol^# 25-hydroxycholecalciferol Calcitriol (1,25-dihydroxycholecalciferol) Calcitroic acid D₄ Dihydroergocalciferol D₅ D analogues Alfacalcidol Dihydrotachysterol Calcipotriol Tacalcitol Paricalcitol
E	Tocopherol Alpha Beta Gamma Delta Tocotrienol Alpha Beta Gamma Delta Tocofersolan
K	Naphthoquinone Phylloquinone (K₁)^# Menaquinones (K₂) Menadione (K₃)^‡ Various (K₄) 4-Amino-2-methyl-1-naphthol (K₅)^‡ 2-Methylnaphthalene-1,4-diamine (K₆) 4-Amino-3-methyl-1-naphthol (K₇)

Water
soluble

Combinations

Multivitamins

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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