This is a transliteration of the Hebrew word כְּרֻבִים that refers to a rank of angelic beings ("cherubim").

Notice the construction of this word.

ἄνωθεν (as in John 3:3) can mean either "from above" (ἄνω = up; -θεν = from) or "again." The prefix ἐπάν(ο)- means "again." ἐπανέρχομαι and ἐπανιέναι ("come [back] again"). In this case, there is an alpha privative (ἀ[ν]- ἐπάν- = not back).

The adjective then means "not to come back, not to return, not to be brought back."

This is also seen in the word ἐπάνοδος "way back" above.

If we interpret the text metaphorically, this is what I get:

The intermediate education (Hagar) met the divine reason (the Logos) and was brought back to the ruling virtue (Sarah) the first time that it abandoned virtue (moral worth). The second time that this happened, it was cast away never to return.

This seems to refer to some historical event in which those in charge of "the intermediate instruction" abandoned "the ruling virtue." It seems to me to refer to times when the teachers of Torah left off teaching the moral backstory of the text in favor of a literal interpretation of the Bible. At one point, those who had been teaching the literal meaning of the text eventually came back to teaching the "real" meaning behind it; but, apparently in the time of Philo, people had gone back to teaching the literal meaning, which Philo thought caused them to be permanently disconnected from the real intention of the text.

I wonder what he might be referring to historically. Any ideas?

"he is not kept from happening upon a way back."

The verb τυγχάνω can seem strange in English. It means generally to "hit" or "hit upon." It's as if something happens by chance. It often takes an accusative with a living thing and a genitive with non-living things. In this case, ἐπανόδου is the genitive object of τυχεῖν, which is completing the verb κεκώλυται (that is, the 3s perf pass ind of κωλύω).

Vocab

Reading 1, Verse 2

• ἐπανόδου: fem gen sg
• τυχεῖν: aor act inf
• κεκώλυται: perf mid/pass ind
• ἐκβληθείς: aor pass part masc nom sg
• ἀίδιον: fem acc sg
• φυγήν: fem acc sg
• ὑπομένει: 3s pres act ind
• μήπω: adv
• κραταιῶς: adv from adj κραταιός
• καταληφθέντι: aor pass part masc dat sg
• δέδοται: 3s perf pass ind
• μετανοήσαντι: aor act part masc dat sg
• καθάπερ: particle
• ἐξέπεσε: 3s aor act ind
• κατελθεῖν: aor act inf
• πιεσθένταaor pass part masc acc sg
• ὑποβεβλημένον: perf mid/pass part masc acc sg
• σφοδρᾷ: fem dat sg
• ἀνιάτῳ: masc/fem dat sg
• νόσῳ: fem dat sg
• μέχρι: prep
• σκορακισθέντα: aor pass part masc acc sg
• ἀσεβῶν: masc gen pl
• χῶρον: masc acc sg
• ἄκρατον: masc/fem acc sg
• συνεχῆ: masc/fem acc sg
• βαρυδαιμονίαν: fem acc sg

Vocab

Reading 1, Verse 1

• κατῴκισεν: 2s aor ind act
• ἀπέναντι: prep (+ gen)
• τρυφῆς: fem gen sg
• Χερουβίμ: translit of Hebrew כְּרֻבִים [kᵉrūḇîm]
• φλογίνην: fem acc sg
• ῥομφαίαν: fem acc sg
• στρεφομένην: pres mid/pass part fem acc sg
• νῦν: in this context, "in this verse"
• πρότερον: in this context, "in the previous verse"
• παρέργως: adv
• θείς: aor act part masc nom sg
• εἰδώς: perf act ind masc nom sg
• κυρίως: adv from adj κύριος
• εὐθυβόλως: adv from adj εὐθύβολος

Given the definiteness of the expression (also in Hebrew: לַ֫הַט הַחֶ֫רֶב הַמִּתְהַפֶּ֫כֶת) we are led to think that we should know what this sword is, that it was possibly a commonly known thing in the Ancient Near East. Do you think that this is possible?

This word is composed of the alpha privative and the root for "healing," which is where my name comes from! ἰάομαι (pres mid) takes the future in the active, the participle of which is ἰάσων, meaning something like "being about to heal." Therefore, ἀνίατος is something that is incurable. It may refer to wickedness that cannot be atoned for, to a person who is unforgivably evil.

"he suffers the everlasting banishment."

Here we have a contrast between someone who is "sent away" (using the verb (ἐξ)αποστέλλω) and someone who is "cast out" (using the verb ἐκβάλλω). One has the option to return, while the other doesn't. Philo is going to interpret this repetition of man being sent/cast out of the garden in connection to Hagar being sent away twice - the first time from which she returned, and the second time at which she was kept from returning. Sarah is interpreted as "sovereign virtue" (ἡ ἄρχουσα ἀρετή), given that "Sarah" is related to "minister" or "ruler" in Hebrew (שר > שרה).

Someone who is not completely controlled by evil has the option to return, but someone who has been cast out (excommunicated?) doesn't have the option of return. Adam was not given the option of return, which is illustrated by the verb used (ἐκβάλλω) and the placement of the guard (cherubim with the spinning fiery sword).

Because of how Philo interprets this section, we should imagine the words καὶ ἔταξε as missing from the verse, and the verb κατῴκισεν as governing the compound object τὰ Χερουβὶμ καὶ τὴν φλογίνην ῥομφαίαν. In other words, God ἐξέβαλε ("expelled") Adam and κατῴκισεν ("placed") the cherubim and the flaming sword. The Hebrew text agrees with Philo's understanding in making "the Cherubim" and "the spinning flaming sword" the object of the second verb (וישכן). The LXX as we have it today added a third verb (ἔταξε) to the mix.

MT: וַיַּשְׁכֵּן מִקֶּ֫דֶם לְגַן עֵ֫דֶן אֶת-הַכְּרֻבִים וְאֵת לַ֫הַט הַחֶ֫רֶב הַמִּתְהַפֶּ֫כֶת לִשְׁמֹר אֶת-דֶּ֫רֶךְ עֵץ הַחַיִּים

Reading 1, Verse 1

• κατῴκισεν: 2s aor ind act
• ἀπέναντι: prep (+ gen)
• τρυφῆς: fem gen sg
• Χερουβίμ: translit of Hebrew כְּרֻבִים [kᵉrūḇîm]
• φλογίνην: fem acc sg
• ῥομφαίαν: fem acc sg
• στρεφομένην: pres mid/pass part fem acc sg
• νῦν: in this context, "in this verse"
• πρότερον: in this context, "in the previous verse"
• παρέργως: adv
• θείς: aor act part masc nom sg
• εἰδώς: perf act ind masc nom sg
• κυρίως: adv from adj κύριος
• εὐθυβόλως: adv from adj εὐθύβολος

This passage makes it seem like ἡ φλογίνη ῥομφαία ἡ στρεφομένη is something that we should probably know from another story or another context. However, it wasn't brought up before this verse and never makes an appearance again. What's the point of this spinning fiery sword?

ὁ παράδεισος τῆς τρυφῆς is used a few times in this section as a reference to the garden of Eden. In fact, the Hebrew text here says וַיַּשְׁכֵּן מִקֶּדֶם לְגַן-עֵדֶן wayyaškēn miqqéḏem lᵉḡan-ʿḗḏen and he settled [him] to the east of the garden of Eden. The entire phrase "garden of Eden" has been changed to ὁ παράδεισος τῆς τρυφῆς. He interpreted "Eden" as τρυφή.

The word χερουβίμ comes from Hebrew כְּרוּבִים‎ kᵉrûḇîm. It's interesting that cherub in English uses the [č] (that is, [ʧ] in the IPA) sound at the beginning (like the ch in child) and χερούβ in Greek uses the [χ] sound in the same position, when the Hebrew כּ is hard, like the k in English. I wonder what this shows us about transliterations from Hebrew into Greek as used in the Septuagint (LXX) and the Koine.

The subject is still ὁ θεός. In the actual quote from the LXX, the object of the verb is explicit (αὐτόν), referring to Adam. It says that God expelled Adam and settled him opposite Eden. Philo seems to intentionally read the passage differently, taking τὰ Χερουβίμ as the object of this verb. Similarly, the phrase καὶ ἔταξε has been deleted in Philo's text, since they are not necessary given how he understood κατῴκισεν.

The implied subject here is ὁ θεός. This is the beginning of a quotation pulled from Genesis 3:24.